Can you create a, a sheet of organic chemistry, uh, and the chapter is heterocycle compound? Okay. In that sheet, you have to, like, give me the structure of those, these compounds, um, and their medicinal uses. And your main focus will be, mm, five, uh, compound, mm, which you have to provide me, uh, with the... Mm-hmm. ... synthesis, chemical reaction, medicinal uses. Yeah, this, this much. And the compounds are, uh, pyrazole, imidazole, oxazole, thiazole, pyridine, quinoline, isoquinoline, acrylidine. Are you in- in doubt? Indole. Mmm, uh, pyrimidine, purine, azepines. These are the compound, and the main focus of compound will be the, uh, pyrazole, imidazole, pyridine, quinoline, pyrimidine.
Reading File
Finding Sources
Finding Sources
Finding Sources
Reading File
Reading File
Searching the Web
heterocyclic compounds pyrazole imidazole oxazole thiazole synthesis medicinal uses organic chemistry
Reading Web Page
https://copbela.org/downloads/2023/SELF%20LEARNING%20MATERIA…
Searching the Web
pyridine quinoline pyrimidine purine indole synthesis reactions medicinal uses pharmacy heterocyclic
Running Command
mkdir -p /home/daytona/workspace/heterocyclic-chemistry && ls /home/daytona/work…
Writing File
~/heterocyclic-chemistry/build_pptx.js
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pres.layout = 'LAYOUT_WIDE'; // 13.3" x 7.5"
pres.title = 'Heterocyclic Compounds - Organic Chemistry';
pres.author = 'Orris AI';
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// ═══════════════════════════════════════════════════════════════
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// ═══════════════════════════════════════════════════════════════
// SLIDE 2: OVERVIEW / CLASSIFICATION
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['Pyrazole','2N (1,2-pos)','C₃H₄N₂','Colorless solid, aromatic'],
['Imidazole','2N (1,3-pos)','C₃H₄N₂','Amphoteric, more basic'],
['Oxazole','N + O','C₃H₃NO','Electron poor'],
['Thiazole','N + S','C₃H₃NS','Colorless liquid'],
['Indole','Benzene + pyrrole','C₈H₇N','Bicyclic, fused'],
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['Isoquinoline','Benzene + pyridine (iso)','C₉H₇N','More basic than quinoline'],
['Acridine','Dibenzo + pyridine','C₁₃H₉N','Tricyclic system'],
['Pyrimidine','2N (1,3-pos)','C₄H₄N₂','Less basic than pyridine'],
['Purine','Pyrimidine + imidazole','C₅H₄N₄','Bicyclic, in DNA/RNA'],
['Azepine','1N, 7-membered','C₆H₇N','Non-aromatic ring'],
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footerBar(sl, 'Classification Overview');
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// ═══════════════════════════════════════════════════════════════
// SLIDE 3 ★ PYRAZOLE (MAIN FOCUS)
// ═══════════════════════════════════════════════════════════════
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sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'F8FFF8'}});
addHeader(sl, '★ Pyrazole (C₃H₄N₂) — Five-Membered, Diazole', 'MAIN FOCUS COMPOUND | Contains N at positions 1 & 2');
// STAR badge
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// Structure box
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'N─N Ring',
'Five-membered ring\nN at positions 1 & 2\nC₃H₄N₂ | MW = 68.08\npKa = 2.52 (base), 14.2 (acid)\nAromatic (6π electrons)\nExhibits tautomerism (1H ↔ 2H)',
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// Ring diagram text representation
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// Physical properties
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'Colorless solid, pleasant smell',
'Mp: 70°C, Bp: 187°C',
'Soluble in water, EtOH, ether',
'Aromatic (6π e⁻ system)',
'Exhibits tautomerism',
'pKa 2.52 (conjugate acid)',
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// Synthesis
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'1. From 1,3-Dicarbonyl Compounds:',
' 1,3-Dicarbonyl + Hydrazine → Pyrazole + 2H₂O',
' (Knorr pyrazole synthesis)',
'2. From 1,3-Dipolar Compounds:',
' Diazo compound + Acetylenic derivative → Pyrazole',
'3. Cyclocondensation of hydrazone with acetylene',
'4. From pyridazines via ring contraction',
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// Chemical Reactions
addContentBox(sl, 3.5, 4.05, 4.5, 2.8, 'Chemical Reactions', [
'1. Oxidation: Resistant; side chains oxidized by KMnO₄ → COOH',
'2. Reduction: Ring reduced by H₂/Pt or Na/EtOH → pyrazoline',
'3. Electrophilic Substitution: Occurs at C-4 (most activated)',
'4. N-Alkylation: N-1 alkylated by alkyl halides',
'5. N-Acylation: Forms N-acylpyrazoles',
'6. Halogenation: Br₂ in AcOH → 4-bromopyrazole',
'7. Nitration: HNO₃/H₂SO₄ → 4-nitropyrazole',
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// Medicinal Uses
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'1. Anti-inflammatory & Analgesic:',
' • Phenylbutazone (pyrazolone) – NSAIDs',
' • Antipyrine (phenazone) – analgesic/antipyretic',
' • Oxyphenbutazone – anti-inflammatory',
'',
'2. Antidiabetic:',
' • Pyrazole nucleus in SGLT-2 inhibitors',
'',
'3. Anticancer:',
' • Crizotinib, Ruxolitinib contain pyrazole ring',
' • Pyrazolo[3,4-d]pyrimidines as kinase inhibitors',
'',
'4. Antibacterial/Antifungal:',
' • Several pyrazole derivatives show MIC activity',
'',
'5. Antiviral:',
' • Lonafarnib derivatives',
'',
'6. Agrochemistry:',
' • Fipronil insecticide (pyrazole core)',
' • Fenpyroximate acaricide',
'',
'7. Veterinary: Deracoxib (COX-2 inhibitor)',
], C.red, 'FEF9E7');
footerBar(sl, '★ MAIN FOCUS: Pyrazole');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 4 ★ IMIDAZOLE (MAIN FOCUS)
// ═══════════════════════════════════════════════════════════════
{
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addHeader(sl, '★ Imidazole (C₃H₄N₂) — Five-Membered, 1,3-Diazole', 'MAIN FOCUS COMPOUND | Isomeric with Pyrazole | Found in histidine & purine');
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'N1-C2-N3 Ring',
'Five-membered ring\nN at positions 1 & 3 (1,3-diazole)\nC₃H₄N₂ | MW = 68.08\npKa = 6.95 — more basic than pyrazole\nAromatic, amphoteric\nPresent in histidine amino acid',
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addContentBox(sl, 0.3, 4.35, 3.2, 2.5, 'Physical Properties', [
'Colorless solid, Mp: 89-91°C',
'Bp: 257°C',
'Highly soluble in water',
'Amphoteric (acid & base)',
'More basic than pyrazole (pKa 6.95)',
'Exhibits tautomerism (1H ↔ 3H)',
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addContentBox(sl, 3.7, 1.1, 4.5, 2.85, 'Synthesis Methods', [
'1. Debus-Radziszewski Synthesis:',
' Glyoxal + Aldehyde + NH₃ → Imidazole',
'2. From α-Aminocarbonyl Compounds:',
' α-haloketone + amidine → imidazole',
'3. Van Leusen Synthesis:',
' TosMIC + imine → 1,5-disubstituted imidazoles',
'4. Cyclization of formamide with HCHO & NH₃',
'5. From 1,2-dicarbonyl + formaldehyde + amine',
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addContentBox(sl, 3.7, 4.05, 4.5, 2.8, 'Chemical Reactions', [
'1. Electrophilic Subst: Attack at C-4/C-5 (not C-2)',
'2. Nitration: conc. HNO₃/H₂SO₄ → 4-nitroimidazole',
'3. Halogenation: Br₂ → 4-bromoimidazole',
'4. N-Alkylation: Both N atoms can be alkylated',
'5. N-Acylation: Reacts with acid chlorides at N-1',
'6. Reduction: H₂/Raney Ni → 4,5-dihydroimidazole',
'7. With acids: forms stable salts (imidazolium)',
], C.purple, 'F5EEF8');
addContentBox(sl, 8.4, 1.1, 4.6, 5.75, 'Medicinal Uses & Examples', [
'1. Antifungal Agents (azole antifungals):',
' • Clotrimazole, Miconazole, Econazole',
' • Ketoconazole – broad spectrum antifungal',
' • Mechanism: inhibit CYP51 (ergosterol synthesis)',
'',
'2. Antibacterial:',
' • Metronidazole (nitroimidazole) – antiprotozoal',
' • Tinidazole – giardiasis, amoebiasis',
'',
'3. Proton Pump Inhibitors:',
' • Omeprazole, Pantoprazole – contain imidazole',
'',
'4. Antihistamines:',
' • Histamine itself has imidazole ring',
' • H2-blockers: Cimetidine (imidazole ring)',
'',
'5. Antihypertensive:',
' • Clonidine – imidazoline derivative',
'',
'6. General Anesthesia:',
' • Etomidate – imidazole carboxylate',
'',
'7. Antiviral: Ribavirin (imidazole nucleoside)',
], C.orange, 'FEF9E7');
footerBar(sl, '★ MAIN FOCUS: Imidazole');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 5: OXAZOLE & THIAZOLE
// ═══════════════════════════════════════════════════════════════
{
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sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'FAFAFA'}});
addHeader(sl, 'Oxazole & Thiazole — Five-Membered Heterocycles', 'Oxazole (N+O) | Thiazole (N+S) | Both have ring numbering from heteroatom');
// OXAZOLE LEFT
sl.addShape(pres.ShapeType.rect, {x:0.25, y:1.05, w:6.3, h:6.15, fill:{color:'FFFDE7'}, line:{color:C.accentGold,width:2}});
sl.addShape(pres.ShapeType.rect, {x:0.25, y:1.05, w:6.3, h:0.38, fill:{color:C.accentGold}});
sl.addText('OXAZOLE (C₃H₃NO | MW 69.06)', {x:0.25,y:1.05,w:6.3,h:0.38,fontSize:13,bold:true,color:C.darkBlue,align:'center',valign:'middle',margin:0});
addContentBox(sl, 0.4, 1.55, 3.0, 1.6, 'Structure & Properties', [
'Formula: C₃H₃NO | 1,3-Oxazole',
'N at pos 3, O at pos 1',
'pKa = 0.8 (weakly basic)',
'Less reactive than imidazole',
'Colorless liquid, fishy odor',
], C.accentGold, 'FFF8E1');
addContentBox(sl, 3.5, 1.55, 3.0, 1.6, 'Synthesis', [
'1. Robinson-Gabriel synthesis:',
' α-Acylaminocarbonyl cpd → oxazole',
'2. Cyclodehydration of β-hydroxy amides',
'3. Fischer oxazole synthesis:',
' α-haloketone + formamide → oxazole',
'4. From amino acids + acid chlorides',
], C.accentGold, 'FFF8E1');
addContentBox(sl, 0.4, 3.25, 6.1, 1.75, 'Chemical Reactions', [
'1. Electrophilic Substitution: preferred at C-5 position',
'2. More reactive than thiazole, less than imidazole',
'3. Ring opening with strong bases (C-2 position)',
'4. Cycloaddition reactions (Diels-Alder with dienes)',
'5. Nucleophilic attack at C-2 (electrophilic carbon)',
], C.accentGold, 'FFFDE7');
addContentBox(sl, 0.4, 5.1, 6.1, 2.0, 'Medicinal Uses', [
'• Broad biological activities: antibacterial, antifungal, antiviral',
'• Antitubercular agents (oxazole ring in drugs)',
'• Anticancer activity in oxazoline derivatives',
'• Anti-inflammatory: oxicam NSAIDs (piroxicam, meloxicam)',
'• Oxazolidinone antibiotics: Linezolid, Tedizolid',
'• Cycloserine (antitubercular) – isoxazoline type',
], C.accentGold, 'FFF3CD');
// THIAZOLE RIGHT
sl.addShape(pres.ShapeType.rect, {x:6.8, y:1.05, w:6.25, h:6.15, fill:{color:'F0FFF4'}, line:{color:C.teal,width:2}});
sl.addShape(pres.ShapeType.rect, {x:6.8, y:1.05, w:6.25, h:0.38, fill:{color:C.teal}});
sl.addText('THIAZOLE (C₃H₃NS | MW 85.13)', {x:6.8,y:1.05,w:6.25,h:0.38,fontSize:13,bold:true,color:C.white,align:'center',valign:'middle',margin:0});
addContentBox(sl, 6.95, 1.55, 3.0, 1.6, 'Structure & Properties', [
'Formula: C₃H₃NS | 1,3-Thiazole',
'N at pos 3, S at pos 1',
'pKa = 2.5 (less basic than imidazole)',
'Colorless liquid, pyridine odor',
'Intermediate reactivity',
], C.teal, 'E8F8F5');
addContentBox(sl, 10.05, 1.55, 2.9, 1.6, 'Synthesis', [
'1. Hantzsch Thiazole Synthesis:',
' α-halocarbonyl + thioamide → thiazole',
'2. From thioacetamide + α-haloketone',
'3. Cook-Heilbron synthesis',
'4. Gabriel-Colman rearrangement',
], C.teal, 'E8F8F5');
addContentBox(sl, 6.95, 3.25, 6.1, 1.75, 'Chemical Reactions', [
'1. Electrophilic Subst: at C-5 (less reactive than imidazole)',
'2. N-Alkylation: forms thiazolium salts',
'3. Nucleophilic attack at C-2 (most electrophilic carbon)',
'4. Halogenation: Br₂ → 5-bromothiazole',
'5. Oxidation: S can be oxidized (sulfoxide, sulfone)',
], C.teal, 'EAFAF1');
addContentBox(sl, 6.95, 5.1, 6.1, 2.0, 'Medicinal Uses', [
'• Vitamin B1 (Thiamine) – contains thiazole ring',
'• Antibiotics: Penicillin (thiazolidine ring)',
'• Antibacterial: Sulfathiazole (sulfonamide)',
'• Antifungal: Abafungin',
'• Antiviral: Riluzole (ALS treatment)',
'• Anticancer: Dasatinib (BCR-ABL kinase inhibitor)',
'• Anti-inflammatory: Meloxicam (thiazole NSAIDs)',
], C.teal, 'D5F5E3');
footerBar(sl, 'Oxazole & Thiazole');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 6 ★ PYRIDINE (MAIN FOCUS)
// ═══════════════════════════════════════════════════════════════
{
let sl = pres.addSlide();
sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'F0F4F8'}});
addHeader(sl, '★ Pyridine (C₅H₅N) — Six-Membered, Monoaza-benzene', 'MAIN FOCUS COMPOUND | Weakly basic liquid | Found in coal tar');
sl.addShape(pres.ShapeType.roundRect, {x:10.5,y:0.1,w:2.6,h:0.7,fill:{color:C.accentGold},rectRadius:0.08});
sl.addText('★ MAIN FOCUS', {x:10.5,y:0.1,w:2.6,h:0.7,fontSize:13,bold:true,color:C.darkBlue,align:'center',valign:'middle',margin:0});
addStructureBox(sl, 0.3, 1.1, 3.2, 2.1,
'Aza-benzene',
'Six-membered ring, N replaces CH\nC₅H₅N | MW = 79.10\npKa = 5.25 (weaker than amines)\nAromatic (6π electrons)\nSp² N, lone pair NOT in π system',
'EBF5FB'
);
// Basicity box (important special topic)
sl.addShape(pres.ShapeType.rect, {x:0.3,y:3.3,w:3.2,h:3.5,fill:{color:'E3F2FD'},line:{color:C.midBlue,width:2}});
sl.addShape(pres.ShapeType.rect, {x:0.3,y:3.3,w:3.2,h:0.35,fill:{color:C.midBlue}});
sl.addText('BASICITY OF PYRIDINE', {x:0.3,y:3.3,w:3.2,h:0.35,fontSize:10,bold:true,color:C.white,align:'center',valign:'middle',margin:0});
sl.addText([
{text:'pKa = 5.25\n', options:{bold:true,fontSize:13,color:C.red,breakLine:true}},
{text:'Weaker than alkylamines (pKa ~10)\n', options:{fontSize:9.5,breakLine:true}},
{text:'Reason: N lone pair is in sp² orbital\n', options:{fontSize:9.5,breakLine:true}},
{text:'(vs sp³ in alkylamines → sp² holds e⁻ tighter)\n', options:{fontSize:9.5,breakLine:true}},
{text:'\nCompared to aniline (pKa 4.6): MORE basic\n', options:{fontSize:9,color:C.teal,breakLine:true}},
{text:'because no resonance delocalization of lone pair\n', options:{fontSize:9,breakLine:true}},
{text:'\nOrder: Alkylamine > Pyridine > Aniline\n', options:{fontSize:10,bold:true,color:C.orange,breakLine:true}},
{text:'~10 5.25 4.6', options:{fontSize:10,bold:true,color:C.orange}},
], {x:0.38,y:3.7,w:3.05,h:2.85,valign:'top',margin:3});
addContentBox(sl, 3.7, 1.1, 4.5, 2.85, 'Synthesis Methods', [
'1. From Coal Tar: light oil fraction treated with dil. H₂SO₄',
'2. Hantzsch Synthesis:',
' β-keto ester + HCHO + NH₃ → dihydropyridine → oxidation → pyridine',
'3. Chichibabin Synthesis:',
' Acetaldehyde + formaldehyde + NH₃ condensation',
'4. Guareschi-Thorpe: aldehyde + keto ester + NH₃',
'5. Kröhnke Synthesis: α-pyridinium salts + α,β-unsaturated carbonyls',
'6. Combes Synthesis: 1,5-diketone + hydroxylamine',
], C.midBlue, 'EBF5FB');
addContentBox(sl, 3.7, 4.05, 4.5, 2.8, 'Chemical Reactions', [
'1. Electrophilic Subst: at C-3 (N deactivates ortho/para)',
'2. Nucleophilic Subst: at C-2 & C-4 (N activates these)',
'3. Chichibabin Reaction: Na/NaNH₂ → 2-aminopyridine',
'4. N-Oxide formation: H₂O₂ → pyridine-N-oxide',
'5. Reduction: H₂/Pt → piperidine',
'6. Halogenation: Br₂ → 3-bromopyridine',
'7. Nitration: HNO₃/H₂SO₄ → 3-nitropyridine',
'8. Sulfonation: Oleum → pyridine-3-sulfonic acid',
], C.purple, 'F5EEF8');
addContentBox(sl, 8.4, 1.1, 4.6, 5.75, 'Medicinal Uses & Examples', [
'1. Vitamins:',
' • Vitamin B3 (Nicotinic acid/Niacinamide)',
' • Vitamin B6 (Pyridoxine) – cofactor in metabolism',
'',
'2. Antimicrobial:',
' • Isoniazid (INH) – first-line anti-TB drug',
' • Pyrazinamide – anti-TB',
' • Ciprofloxacin – contains pyridone ring',
'',
'3. Antihistamines:',
' • Chlorphenamine (pyridine derivative)',
' • Diphenhydramine analogues',
'',
'4. Antihypertensive:',
' • Amlodipine – calcium channel blocker',
' • Nifedipine – dihydropyridine CCB',
'',
'5. CNS Agents:',
' • Nicotine – acetylcholine receptor agonist',
' • Pyridostigmine – acetylcholinesterase inhibitor',
'',
'6. Anticancer:',
' • Imatinib, Erlotinib (contain pyridine ring)',
'',
'7. Local Anesthetic: Cetylpyridinium chloride',
], C.teal, 'E8F8F5');
footerBar(sl, '★ MAIN FOCUS: Pyridine | Basicity Order: Alkylamine > Pyridine > Aniline');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 7 ★ QUINOLINE (MAIN FOCUS)
// ═══════════════════════════════════════════════════════════════
{
let sl = pres.addSlide();
sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'FFF8F0'}});
addHeader(sl, '★ Quinoline (C₉H₇N) — Benzo[b]pyridine / Benzopyridine', 'MAIN FOCUS COMPOUND | Fused bicyclic | Important antimalarial scaffold');
sl.addShape(pres.ShapeType.roundRect, {x:10.5,y:0.1,w:2.6,h:0.7,fill:{color:C.accentGold},rectRadius:0.08});
sl.addText('★ MAIN FOCUS', {x:10.5,y:0.1,w:2.6,h:0.7,fontSize:13,bold:true,color:C.darkBlue,align:'center',valign:'middle',margin:0});
addStructureBox(sl, 0.3, 1.1, 3.2, 2.1,
'Benzene + Pyridine',
'Bicyclic: benzene fused to pyridine\nN at position 1\nC₉H₇N | MW = 129.16\npKa = 4.85 (weaker than pyridine)\nColorless hygroscopic oil\nFluorescent; isolated from coal tar',
'FFF3E0'
);
addContentBox(sl, 0.3, 3.3, 3.2, 3.5, 'Physical Properties & Occurrence', [
'Colorless oily liquid, bad smell',
'Bp: 238°C, Mp: -15°C',
'Hygroscopic — absorbs moisture',
'Fluorescent compound',
'Isolated from coal tar',
'More basic than acridine, less than isoquinoline',
'Found in tobacco smoke',
'Constituent of many alkaloids',
], C.orange, 'FFF8E1');
addContentBox(sl, 3.7, 1.1, 4.5, 2.85, 'Synthesis Methods', [
'1. Skraup Synthesis (CLASSIC):',
' Aniline + glycerol + H₂SO₄ + oxidant → quinoline',
'2. Doebner-Miller Synthesis:',
' Aniline + α,β-unsaturated ketone/aldehyde → quinoline',
'3. Combes Synthesis:',
' Aniline + 1,3-diketone → HCl → 2,4-disubstituted quinoline',
'4. Conrad-Limpach Synthesis:',
' Aniline + β-keto ester → 4-hydroxyquinoline',
'5. Niementowski Synthesis:',
' Anthranilic acid + carbonyl cpd → quinoline',
], C.orange, 'FFF3E0');
addContentBox(sl, 3.7, 4.05, 4.5, 2.8, 'Chemical Reactions', [
'1. Electrophilic Subst: at C-5 and C-8 (benzene ring)',
'2. Nucleophilic Subst: at C-2 and C-4 (pyridine ring)',
'3. N-Oxide: H₂O₂/peracid → quinoline-N-oxide',
'4. Reduction: H₂/Pt → 1,2-dihydroquinoline',
'5. Quaternization: CH₃I → N-methylquinolinium iodide',
'6. Halogenation: Br₂ → 3-bromoquinoline',
'7. Nitration: HNO₃/H₂SO₄ → 5-nitroquinoline (mainly)',
'8. Bischler-Napieralski for isoquinoline (related)',
], C.red, 'FEE9E9');
addContentBox(sl, 8.4, 1.1, 4.6, 5.75, 'Medicinal Uses & Examples', [
'1. Antimalarial Agents (MAJOR USE):',
' • 4-Aminoquinolines: Chloroquine, Hydroxychloroquine',
' • Amodiaquine – antimalarial',
' • Mefloquine – multidrug-resistant malaria',
' • Cinchona alkaloids: Quinine, Quinidine',
' • 8-Aminoquinolines: Primaquine (radical cure)',
'',
'2. Antibacterial:',
' • Fluoroquinolones (quinolone core):',
' • Ciprofloxacin, Levofloxacin, Norfloxacin',
' • Moxifloxacin – broad-spectrum',
'',
'3. Anti-arrhythmic:',
' • Quinidine – class IA antiarrhythmic',
'',
'4. Local Anesthetic:',
' • Dibucaine (quinoline derivative)',
'',
'5. Antiseptic:',
' • Chlorquinaldol, Halquinol',
'',
'6. Anticancer: Camptothecin analogues',
' (topoisomerase I inhibitors)',
], C.midBlue, 'EBF5FB');
footerBar(sl, '★ MAIN FOCUS: Quinoline | Skraup Synthesis is CLASSIC');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 8: ISOQUINOLINE & ACRIDINE
// ═══════════════════════════════════════════════════════════════
{
let sl = pres.addSlide();
sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'FAFAFA'}});
addHeader(sl, 'Isoquinoline & Acridine — Bicyclic & Tricyclic Heterocycles', 'Isoquinoline (Benzo[c]pyridine) | Acridine (Dibenzo[b,e]pyridine)');
// ISOQUINOLINE
sl.addShape(pres.ShapeType.rect, {x:0.25,y:1.05,w:6.3,h:6.15,fill:{color:'F5EEF8'},line:{color:C.purple,width:2}});
sl.addShape(pres.ShapeType.rect, {x:0.25,y:1.05,w:6.3,h:0.38,fill:{color:C.purple}});
sl.addText('ISOQUINOLINE (C₉H₇N | MW 129.16)', {x:0.25,y:1.05,w:6.3,h:0.38,fontSize:13,bold:true,color:C.white,align:'center',valign:'middle',margin:0});
addContentBox(sl, 0.4, 1.55, 2.8, 1.55, 'Structure', [
'N at position 2 (unlike quinoline N-1)',
'Benzene fused to pyridine (benzo[c])',
'pKa = 5.4 — MORE basic than quinoline',
'Colorless solid, Mp: 26°C',
'Present in opium alkaloids',
], C.purple, 'F5EEF8');
addContentBox(sl, 3.3, 1.55, 3.1, 1.55, 'Synthesis', [
'1. Bischler-Napieralski:',
' β-arylethylamine + acid chloride → cyclization',
'2. Pictet-Spengler:',
' β-arylethylamine + aldehyde → isoquinoline',
'3. Pomeranz-Fritsch:',
' Benzaldehyde + aminoacetal → ring closure',
], C.purple, 'F5EEF8');
addContentBox(sl, 0.4, 3.2, 5.95, 1.65, 'Chemical Reactions', [
'1. Electrophilic Subst: at C-5 & C-8 (benzene ring)',
'2. Nucleophilic Subst: at C-1 (more susceptible than quinoline)',
'3. Reduction: NaBH₄ → 1,2-dihydroisoquinoline',
'4. N-Oxidation: m-CPBA → isoquinoline-N-oxide',
'5. Quaternization: alkyl halides → isoquinolinium salts',
], C.purple, 'EDE0F0');
addContentBox(sl, 0.4, 4.95, 5.95, 2.1, 'Medicinal Uses', [
'• Opium alkaloids: Papaverine (isoquinoline) – antispasmodic',
'• Narcotine (Noscapine) – antitussive, anticancer research',
'• Berberine – antimicrobial, antidiarrheal',
'• Tubocurarine – muscle relaxant (curare alkaloid)',
'• Emetine – antiprotozoal (amoebiasis)',
'• Colchicine (modified) – gout treatment',
'• Morphine-related: codeine (benzylisoquinoline backbone)',
], C.purple, 'EDE0F0');
// ACRIDINE
sl.addShape(pres.ShapeType.rect, {x:6.8,y:1.05,w:6.25,h:6.15,fill:{color:'FFF0E6'},line:{color:C.orange,width:2}});
sl.addShape(pres.ShapeType.rect, {x:6.8,y:1.05,w:6.25,h:0.38,fill:{color:C.orange}});
sl.addText('ACRIDINE (C₁₃H₉N | MW 179.22)', {x:6.8,y:1.05,w:6.25,h:0.38,fontSize:13,bold:true,color:C.white,align:'center',valign:'middle',margin:0});
addContentBox(sl, 6.95, 1.55, 2.9, 1.55, 'Structure', [
'Tricyclic: two benzene rings + pyridine',
'N at position 10 (central)',
'pKa = 5.6',
'Colorless solid, Mp: 111°C',
'Strong fluorescence (blue-violet)',
], C.orange, 'FFF0E6');
addContentBox(sl, 9.95, 1.55, 3.0, 1.55, 'Synthesis', [
'1. Bernthsen Synthesis:',
' Diphenylamine + carboxylic acid + ZnCl₂ → acridine',
'2. Leimbach-Schwarzkopf:',
' Diphenylamine + CCl₄/AlCl₃',
'3. Baeyer Synthesis: condensation of aniline with aldehydes',
], C.orange, 'FFF0E6');
addContentBox(sl, 6.95, 3.2, 5.95, 1.65, 'Chemical Reactions', [
'1. Electrophilic Subst: C-2 & C-7 positions (far from N)',
'2. Nucleophilic Subst: C-9 (most reactive toward nucleophiles)',
'3. N-Oxide formation; quaternary salt formation',
'4. Reduction: acridane (9,10-dihydroacridine)',
'5. Diels-Alder reactions at 9,10 positions',
], C.orange, 'FFF3E0');
addContentBox(sl, 6.95, 4.95, 5.95, 2.1, 'Medicinal Uses', [
'• Acriflavine, Proflavine – antiseptic/antibacterial',
'• Quinacrine (Mepacrine) – antimalarial, antiprotozoal',
'• Amsacrine – anticancer (DNA intercalator)',
'• Tacrine – first acetylcholinesterase inhibitor (Alzheimers)',
'• 9-Aminoacridine – intercalating antiseptic',
'• Acridine orange – fluorescent staining dye in microscopy',
], C.orange, 'FFF3CD');
footerBar(sl, 'Isoquinoline & Acridine');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 9: INDOLE
// ═══════════════════════════════════════════════════════════════
{
let sl = pres.addSlide();
sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'F0FFF4'}});
addHeader(sl, 'Indole (C₈H₇N) — Benzo[b]pyrrole | Bicyclic Aromatic', 'Benzene fused with pyrrole ring | E-subst at C-3 | Tryptophan metabolite');
addStructureBox(sl, 0.3, 1.1, 3.2, 2.1,
'Benzo + Pyrrole',
'Bicyclic: benzene fused to pyrrole\nN at position 1 (NH)\nC₈H₇N | MW = 117.15\nWeak acid (pKa ~17, N-H)\nAromatic, planar ring\nPresent in tryptophan structure',
'F0FFF4'
);
addContentBox(sl, 0.3, 3.3, 3.2, 3.5, 'Physical Properties', [
'White crystalline solid',
'Mp: 52-54°C, Bp: 254°C',
'Characteristic smell (jasmine/fecal)',
'Soluble in organic solvents',
'Present in coal tar & flowers',
'N-H is weakly acidic',
'Electrophilic subst at C-3',
], C.teal, 'E8F8F5');
addContentBox(sl, 3.7, 1.1, 4.5, 2.85, 'Synthesis Methods', [
'1. Fischer Indole Synthesis (CLASSIC):',
' Arylhydrazone + acid catalyst → indole',
' (Most widely used method)',
'2. Bischler Synthesis:',
' Aryl amine + haloketone → 2-aryl indole',
'3. Leimgruber-Batcho Synthesis:',
' o-Nitrotoluene + DMF-dimethylacetal → indole',
'4. Reissert Synthesis:',
' o-Nitrotoluene + oxalate → indole',
'5. Madelung Synthesis:',
' N-acyl toluidine + strong base → 2-substituted indole',
], C.teal, 'EAFAF1');
addContentBox(sl, 3.7, 4.05, 4.5, 2.8, 'Chemical Reactions', [
'1. Electrophilic Subst: STRONGLY at C-3 (most reactive)',
'2. Formylation (Vilsmeier): C-3 aldehyde',
'3. Mannich Reaction: C-3 aminomethylation',
'4. Gramine synthesis: indole + HCHO + dimethylamine',
'5. N-Alkylation: with NaH/alkyl halide at N-1',
'6. Reduction: H₂/Pd → 2,3-dihydroindole (indoline)',
' Full reduction → octahydroindole',
'7. Oxidation: O₃ or peroxy acid → oxindole / isatogens',
], C.midBlue, 'EBF5FB');
addContentBox(sl, 8.4, 1.1, 4.6, 5.75, 'Medicinal Uses & Examples', [
'1. Neurotransmitter Precursors:',
' • Tryptophan → Serotonin (5-HT) – mood regulation',
' • Melatonin – sleep regulation (indole amine)',
'',
'2. Analgesic / Anti-inflammatory:',
' • Indomethacin – NSAID (indole acetic acid)',
' • Etodolac – COX-2 selective NSAID',
' • Sulindac – anti-inflammatory',
'',
'3. Anticancer:',
' • Cancer prevention: cruciferous vegetable indoles',
' • Vincristine, Vinblastine (vinca alkaloids) – antimitotic',
' • Sunitinib – kinase inhibitor (indole ring)',
'',
'4. Antihypertensive / Cardiac:',
' • Pindolol – β-blocker (indole ring)',
'',
'5. Antimigraine:',
' • Triptans (Sumatriptan) – 5-HT1B/1D agonist',
'',
'6. Antifungal: Indole alkaloids (various)',
'',
'7. Tryptamine derivatives: psilocybin (psychedelic)',
], C.orange, 'FEF9E7');
footerBar(sl, 'Indole | Fischer Synthesis is CLASSIC | E-Subst at C-3');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 10 ★ PYRIMIDINE (MAIN FOCUS)
// ═══════════════════════════════════════════════════════════════
{
let sl = pres.addSlide();
sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'F8F0FF'}});
addHeader(sl, '★ Pyrimidine (C₄H₄N₂) — Six-Membered, 1,3-Diazine', 'MAIN FOCUS COMPOUND | DNA/RNA bases | N at 1,3 positions | Parent of cytosine, uracil, thymine');
sl.addShape(pres.ShapeType.roundRect, {x:10.5,y:0.1,w:2.6,h:0.7,fill:{color:C.accentGold},rectRadius:0.08});
sl.addText('★ MAIN FOCUS', {x:10.5,y:0.1,w:2.6,h:0.7,fontSize:13,bold:true,color:C.darkBlue,align:'center',valign:'middle',margin:0});
addStructureBox(sl, 0.3, 1.1, 3.2, 2.1,
'N1-C2-N3 Diazine',
'Six-membered ring, N at 1 & 3 positions\nC₄H₄N₂ | MW = 80.09\npKa = 1.3 (less basic than pyridine)\nAromatic (6π electrons)\nParent ring: cytosine, uracil, thymine',
'F8F0FF'
);
addContentBox(sl, 0.3, 3.3, 3.2, 3.5, 'DNA/RNA Pyrimidine Bases', [
'CYTOSINE (C):',
' 4-Aminopyrimidin-2(1H)-one',
' Pairs with Guanine in DNA',
'',
'URACIL (U):',
' Pyrimidine-2,4(1H,3H)-dione',
' RNA only, pairs with Adenine',
'',
'THYMINE (T):',
' 5-Methyluracil',
' DNA only, pairs with Adenine',
], C.purple, 'F5EEF8');
addContentBox(sl, 3.7, 1.1, 4.5, 2.85, 'Synthesis Methods', [
'1. Pinner Synthesis (CLASSIC):',
' Malonic ester + urea/guanidine → pyrimidine',
'2. From 1,3-Dicarbonyl + Amidine:',
' β-Keto ester + amidine → 2-aminopyrimidine',
'3. Shaw-Wheeler synthesis:',
' Condensation of acetamidine with β-chlorovinyl carbonyl',
'4. Cyclization of 1,3-diketone + urea (heat)',
'5. Microwave-assisted synthesis of pyrimidine derivatives',
], C.purple, 'F5EEF8');
addContentBox(sl, 3.7, 4.05, 4.5, 2.8, 'Chemical Reactions', [
'1. Electrophilic Subst: at C-5 (less reactive than benzene)',
'2. Nucleophilic Subst: at C-2, C-4, C-6 (positions bearing N)',
'3. Halogenation: Br₂/AcOH → 5-bromopyrimidine',
'4. Nitration: very harsh conditions → 5-nitropyrimidine',
'5. N-Oxide formation: mCPBA → N-1 or N-3 oxide',
'6. Reduction: NaBH₄ reduces enamine functionality',
'7. Hydrolysis: 2-halopyrimidines → 2-hydroxypyrimidines',
], C.midBlue, 'EBF5FB');
addContentBox(sl, 8.4, 1.1, 4.6, 5.75, 'Medicinal Uses & Examples', [
'1. Antiviral / Anticancer (Nucleoside Analogues):',
' • 5-Fluorouracil (5-FU) – colorectal cancer',
' • Cytarabine (Ara-C) – AML treatment',
' • Gemcitabine – pancreatic cancer',
' • Zidovudine (AZT) – HIV/AIDS (thymine analogue)',
'',
'2. Antimalarial:',
' • Pyrimethamine (DHFR inhibitor)',
' • Trimethoprim – antifolate antibacterial',
'',
'3. Vitamins:',
' • Vitamin B1 (Thiamine) – pyrimidine + thiazole',
'',
'4. Sedative/Hypnotic (Barbiturates):',
' • All barbiturates contain pyrimidine-2,4,6-trione',
' • Phenobarbital, Thiopental, Amobarbital',
'',
'5. Antihypertensive:',
' • Minoxidil – pyrimidine derivative',
'',
'6. Antibacterial:',
' • Sulfadiazine, Sulfamethoxazole – sulfonamides',
'',
'7. Antifungal: Flucytosine (5-FC)',
], C.teal, 'E8F8F5');
footerBar(sl, '★ MAIN FOCUS: Pyrimidine | Pinner Synthesis | DNA bases: Cytosine, Uracil, Thymine');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 11: PURINE & AZEPINE
// ═══════════════════════════════════════════════════════════════
{
let sl = pres.addSlide();
sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'F5FFFE'}});
addHeader(sl, 'Purine & Azepine — Bicyclic & Seven-Membered Heterocycles', 'Purine: Pyrimidine + Imidazole fused | Azepine: 7-membered N-ring');
// PURINE
sl.addShape(pres.ShapeType.rect, {x:0.25,y:1.05,w:6.3,h:6.15,fill:{color:'E8F8F5'},line:{color:C.teal,width:2}});
sl.addShape(pres.ShapeType.rect, {x:0.25,y:1.05,w:6.3,h:0.38,fill:{color:C.teal}});
sl.addText('PURINE (C₅H₄N₄ | MW 120.11)', {x:0.25,y:1.05,w:6.3,h:0.38,fontSize:13,bold:true,color:C.white,align:'center',valign:'middle',margin:0});
addContentBox(sl, 0.4, 1.55, 2.9, 1.8, 'Structure', [
'Bicyclic: pyrimidine + imidazole',
'N at positions 1, 3, 7, 9',
'C₅H₄N₄ | MW = 120.11',
'pKa = 8.9 (weakly basic)',
'Colorless solid',
'Purine bases in DNA: Adenine, Guanine',
], C.teal, 'E8F8F5');
addContentBox(sl, 3.4, 1.55, 3.0, 1.8, 'Synthesis', [
'1. Traube Purine Synthesis:',
' 4,5-diaminopyrimidine + formamide → purine',
'2. From 5-aminoimidazole-4-carboxamide',
'3. Shaw synthesis',
'4. Modified Dimroth synthesis',
'5. De novo (biological): 11-step ring-building',
], C.teal, 'E8F8F5');
addContentBox(sl, 0.4, 3.45, 5.95, 1.5, 'Chemical Reactions', [
'1. Electrophilic Subst: C-8 position (imidazole ring)',
'2. N-Alkylation: N-9 preferentially alkylated in nucleosides',
'3. Oxidation: xanthine oxidase → uric acid (gout)',
'4. Tautomerism between 7H & 9H forms',
], C.teal, 'D5F5E3');
addContentBox(sl, 0.4, 5.05, 5.95, 2.05, 'Medicinal Uses', [
'• Adenine & Guanine: DNA/RNA building blocks',
'• Xanthine → Caffeine (trimethylxanthine) – stimulant',
'• Theophylline – bronchodilator (asthma)',
'• Theobromine – found in chocolate (diuretic)',
'• Allopurinol – xanthine oxidase inhibitor (gout)',
'• Azathioprine – immunosuppressant',
'• Acyclovir, Ganciclovir – antiviral (guanosine analogues)',
'• 6-Mercaptopurine – anticancer (leukemia)',
], C.teal, 'D5F5E3');
// AZEPINE
sl.addShape(pres.ShapeType.rect, {x:6.8,y:1.05,w:6.25,h:6.15,fill:{color:'FFF0F5'},line:{color:C.red,width:2}});
sl.addShape(pres.ShapeType.rect, {x:6.8,y:1.05,w:6.25,h:0.38,fill:{color:C.red}});
sl.addText('AZEPINE (C₆H₇N | MW 93.13)', {x:6.8,y:1.05,w:6.25,h:0.38,fontSize:13,bold:true,color:C.white,align:'center',valign:'middle',margin:0});
addContentBox(sl, 6.95, 1.55, 2.9, 1.8, 'Structure', [
'Seven-membered ring with 1 N',
'C₆H₇N — non-aromatic',
'Unsaturated (various isomers)',
'MW = 93.13',
'Isomers: 1H, 2H, 3H, 4H-azepine',
'Parent of benzodiazepines',
], C.red, 'FFF0F5');
addContentBox(sl, 9.95, 1.55, 2.95, 1.8, 'Synthesis', [
'1. Bamford-Stevens rearrangement',
'2. Ring expansion of pyridine N-oxide',
'3. Diels-Alder + ring modification',
'4. Photochemical isomerization of pyridine',
'5. From cycloheptadienone + NH₃',
], C.red, 'FFF0F5');
addContentBox(sl, 6.95, 3.45, 5.95, 1.5, 'Chemical Reactions', [
'1. Ring expansion from pyridine under UV light',
'2. [3,3]-sigmatropic rearrangements',
'3. Protonation at N → azepinium ions',
'4. Diels-Alder cycloaddition reactions',
], C.red, 'FFDDE4');
addContentBox(sl, 6.95, 5.05, 5.95, 2.05, 'Medicinal Uses (Benzo-fused Azepines)', [
'1. Benzodiazepines (1,4-BZD ring):',
' • Diazepam (Valium) – anxiolytic, anticonvulsant',
' • Lorazepam, Alprazolam – anxiolytics',
' • Clonazepam – antiepileptic',
' • Mechanism: GABA-A receptor positive modulator',
'2. Tricyclic Antidepressants (dibenzazepines):',
' • Imipramine, Clomipramine, Amitriptyline',
'3. Antipsychotics:',
' • Clozapine, Olanzapine (dibenzoazepines)',
], C.red, 'FFDDE4');
footerBar(sl, 'Purine & Azepine | Benzodiazepines are clinically vital azepine derivatives');
}
// ═══════════════════════════════════════════════════════════════
// SLIDE 12: SUMMARY TABLE
// ═══════════════════════════════════════════════════════════════
{
let sl = pres.addSlide();
sl.addShape(pres.ShapeType.rect, {x:0,y:0,w:13.3,h:7.5,fill:{color:'F5F7FA'}});
addHeader(sl, 'Quick Reference Summary — All Heterocyclic Compounds', 'Ring Type | Formula | Key Reactions | Key Medicinal Drugs');
const tableData = [
['Compound', 'Ring', 'Formula', 'Key Synthesis', 'Key Medicinal Drugs'],
['★ Pyrazole', '5-mem, 2N(1,2)', 'C₃H₄N₂', '1,3-Dicarbonyl + Hydrazine', 'Antipyrine, Phenylbutazone, Crizotinib'],
['★ Imidazole', '5-mem, 2N(1,3)', 'C₃H₄N₂', 'Debus-Radziszewski', 'Clotrimazole, Metronidazole, Etomidate'],
['Oxazole', '5-mem, N+O', 'C₃H₃NO', 'Robinson-Gabriel', 'Linezolid, Oxicam NSAIDs'],
['Thiazole', '5-mem, N+S', 'C₃H₃NS', 'Hantzsch Thiazole Synth', 'Thiamine (B1), Penicillin, Dasatinib'],
['★ Pyridine', '6-mem, 1N', 'C₅H₅N', 'Hantzsch / Coal tar', 'INH, Nifedipine, Nicotinic acid'],
['★ Quinoline', '6-mem, benzo+pyr', 'C₉H₇N', 'Skraup Synthesis', 'Chloroquine, Ciprofloxacin, Quinine'],
['Isoquinoline', '6-mem, benzo+pyr(c)', 'C₉H₇N', 'Bischler-Napieralski', 'Papaverine, Berberine, Emetine'],
['Acridine', '6-mem, tricyclic', 'C₁₃H₉N', 'Bernthsen Synthesis', 'Acriflavine, Quinacrine, Tacrine'],
['Indole', '5-mem, benzo+pyrr', 'C₈H₇N', 'Fischer Indole Synth', 'Indomethacin, Sumatriptan, Vincristine'],
['★ Pyrimidine', '6-mem, 2N(1,3)', 'C₄H₄N₂', 'Pinner Synthesis', '5-FU, Barbiturates, Trimethoprim'],
['Purine', 'Bicyclic, 4N', 'C₅H₄N₄', 'Traube Purine Synth', 'Allopurinol, Acyclovir, Caffeine'],
['Azepine', '7-mem, 1N', 'C₆H₇N', 'Ring expansion of pyridine', 'Diazepam, Imipramine, Clozapine'],
];
const cols = [1.5, 1.6, 0.9, 2.85, 3.6];
const startX = 0.2;
const startY = 1.1;
const rowH = 0.46;
const rowColors = ['1B4F72','0D1B2A','1B4F72','0D1B2A','1B4F72','0D1B2A','1B4F72','0D1B2A','1B4F72','0D1B2A','1B4F72','0D1B2A','1B4F72'];
const mainFocus = [1,2,5,6,10]; // indices of main focus rows
tableData.forEach((row, ri) => {
let x = startX;
const isHeader = ri === 0;
const isFocus = mainFocus.includes(ri);
const rowBg = isHeader ? C.darkBlue : (isFocus ? '1A5276' : (ri % 2 === 0 ? 'FFFFFF' : 'EBF5FB'));
const textCol = (isHeader || isFocus) ? C.white : C.textDark;
row.forEach((cell, ci) => {
sl.addShape(pres.ShapeType.rect, {
x, y: startY + ri * rowH, w: cols[ci], h: rowH,
fill: { color: rowBg },
line: { color: 'CCDDEE', width: 0.5 },
});
const isStar = cell.startsWith('★');
sl.addText(cell, {
x: x + 0.05, y: startY + ri * rowH, w: cols[ci] - 0.1, h: rowH,
fontSize: isHeader ? 10 : 9,
bold: isHeader || isFocus,
color: isFocus && !isHeader ? C.accentGold : textCol,
valign: 'middle', margin: 2, wrap: true,
});
x += cols[ci];
});
});
// Legend
sl.addShape(pres.ShapeType.roundRect, {x:0.2,y:7.0,w:4.5,h:0.28,fill:{color:'1A5276'},rectRadius:0.04});
sl.addText('★ = MAIN FOCUS compounds (full synthesis + reactions + uses in detail)', {x:0.3,y:7.0,w:4.4,h:0.28,fontSize:8.5,color:C.accentGold,valign:'middle',margin:0});
footerBar(sl, 'Summary Table — All 13 Heterocyclic Compounds');
}
// ─── WRITE FILE ──────────────────────────────────────────────────
pres.writeFile({ fileName: '/home/daytona/workspace/heterocyclic-chemistry/Heterocyclic_Compounds_Reference_Sheet.pptx' })
.then(() => console.log('DONE: Heterocyclic_Compounds_Reference_Sheet.pptx written successfully'))
.catch(err => { console.error('ERROR:', err); process.exit(1); });
Running Command
cd /home/daytona/workspace/heterocyclic-chemistry && node build_pptx.js
Running Command
ls -lh /home/daytona/workspace/heterocyclic-chemistry/
Your reference sheet is ready! Here's your download link:
Heterocyclic Compounds Reference Sheet
Presentation · PPTX
What's Inside (12 Slides, 483 KB)
Slide 1 - Title Slide
Bold dark-themed cover with all 13 compounds listed and the 5 main focus compounds highlighted.
Slide 2 - Classification Overview
Side-by-side tables: all five-membered vs. six-membered heterocycles with formula, heteroatoms, and key properties.
Slides 3-11 - Individual Compound Slides (each has structure, synthesis, reactions, medicinal uses in color-coded boxes):
| Slide | Compound | Special Notes |
|---|---|---|
| 3 | ★ Pyrazole | Tautomerism, Knorr synthesis, Antipyrine/Crizotinib |
| 4 | ★ Imidazole | Debus-Radziszewski, Azole antifungals, Etomidate |
| 5 | Oxazole + Thiazole | Robinson-Gabriel / Hantzsch, Linezolid, Thiamine, Penicillin |
| 6 | ★ Pyridine | Basicity order (Alkylamine > Pyridine > Aniline), INH, Nifedipine |
| 7 | ★ Quinoline | Skraup synthesis, Chloroquine, Fluoroquinolones |
| 8 | Isoquinoline + Acridine | Bischler-Napieralski, Papaverine, Tacrine |
| 9 | Indole | Fischer synthesis, E-subst at C-3, Indomethacin, Sumatriptan |
| 10 | ★ Pyrimidine | Pinner synthesis, DNA bases, 5-FU, Barbiturates |
| 11 | Purine + Azepine | Traube synthesis, Allopurinol, Benzodiazepines |
Slide 12 - Full Summary Table
All 13 compounds in one table with formula, classic synthesis, and key drugs. Main focus compounds highlighted in gold.
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