Details of CH4214 (Spring 2026)
| Level: 4 | Type: Theory | Credits: 4.0 |
| Course Code | Course Name | Instructor(s) |
|---|---|---|
| CH4214 | Heterocyclic Chemistry and Natural Products | Alakesh Bisai, Sanjio S. Zade |
| Preamble |
|---|
| Part A: Heterocyclic Chemistry:
General reactivity: five and six membered aromatic heterocycles, n-excessive and n-deficient heterocycles, bi- and tricyclic (ring-fused) heterocycles, tautomerism in heterocyclic compounds, metalation and metal-based coupling reactions. (5 Lectures). Five membered heterocycles: Reactions of pyrrole, furan and thiophene (Paal-Knorr, Knorr, Trofimov, Hantzsch, Gewald, Barton-Zard, Feist-Benary, Hinsberg, cycloaddition etc.) and related drugs (ketorolac, tolmetin, clopirac, lipitor, ranitidine, prodigiosin). (7 Lectures) Six membered heterocycles: Reactions of pyridine, pyridone and pyridine N-oxide. (Hantzsch, Guareschi, Bohlmann-Rahtz, Boger, enamide and Vilsmeir, cycloaddition), and related drugs (nifedipine, amlodipine, cerivastatin, ethionamide, fredericamycin, vitamin B 6 ). (3 Lectures) Benzofused 5-membered heterocycle: Reactions of indole (Fischer, Grandberg, Reissert, Bischler, Leimgruber-Batcho, Madelung, Bartoli, Nenitzescu, Gassman, Larock) and related drugs (frovatriptan, almotriptan, rizatriptan, fluvastatin, serotonin etc.). (3 Lectures) Benzofused 6-membered heterocycle: Reactions of quinoline and isoquinoline (Skarup, Friedlander, Pfitzinger, Bischler-Napieralski, Pictel-Gams, Pomeranz-Fritsch etc.) and related drugs (camptothecin, methoxatin, ammosamide, montelukast etc.). (3 Lectures) Three and four-membered heterocycles: Structure, reactions and synthesis. (2 Lectures) Part B: Natural Products: History and Purpose of Synthesis, Milestones in Organic Synthesis, Natural Products and hybrids that Changed the World (4 Lectures) Pharmaceutical Applications of Natural products; Vitamin E, Vitamin K etc. anti-cancer drug Methotrexate, and Taxol (2 Lectures) Importance of Fatty Acid, Terpenes, Steroids, Polyketides and their synthesis, Prostaglandins, Phenolics, Anthraquinones (3 Lectures) Importance and synthetic strategies to Aromatic a-Amino Acids, Lignans, Coumarins, Flavonoids and Antibiotics (5 Lectures) Alkaloids: piperidines, indolizidines, quinolizidines, carbazoles, toxins (nicotine, lupinines, strychnine etc.), drugs (cocaine, opiates, quinine, vincristine etc.) (5 Lectures) |
| Syllabus |
|---|
| Part A: Heterocyclic Chemistry:
General reactivity: five and six membered aromatic heterocycles, n-excessive and n-deficient heterocycles, bi- and tricyclic (ring-fused) heterocycles, tautomerism in heterocyclic compounds, metalation and metal-based coupling reactions. (5 Lectures). Five membered heterocycles: Reactions of pyrrole, furan and thiophene (Paal-Knorr, Knorr, Trofimov, Hantzsch, Gewald, Barton-Zard, Feist-Benary, Hinsberg, cycloaddition etc.) and related drugs (ketorolac, tolmetin, clopirac, lipitor, ranitidine, prodigiosin). (7 Lectures) Six membered heterocycles: Reactions of pyridine, pyridone and pyridine N-oxide. (Hantzsch, Guareschi, Bohlmann-Rahtz, Boger, enamide and Vilsmeir, cycloaddition), and related drugs (nifedipine, amlodipine, cerivastatin, ethionamide, fredericamycin, vitamin B 6 ). (3 Lectures) Benzofused 5-membered heterocycle: Reactions of indole (Fischer, Grandberg, Reissert, Bischler, Leimgruber-Batcho, Madelung, Bartoli, Nenitzescu, Gassman, Larock) and related drugs (frovatriptan, almotriptan, rizatriptan, fluvastatin, serotonin etc.). (3 Lectures) Benzofused 6-membered heterocycle: Reactions of quinoline and isoquinoline (Skarup, Friedlander, Pfitzinger, Bischler-Napieralski, Pictel-Gams, Pomeranz-Fritsch etc.) and related drugs (camptothecin, methoxatin, ammosamide, montelukast etc.). (3 Lectures) Three and four-membered heterocycles: Structure, reactions and synthesis. (2 Lectures) Part B: Natural Products: History and Purpose of Synthesis, Milestones in Organic Synthesis, Natural Products and hybrids that Changed the World (4 Lectures) Pharmaceutical Applications of Natural products; Vitamin E, Vitamin K etc. anti-cancer drug Methotrexate, and Taxol (2 Lectures) Importance of Fatty Acid, Terpenes, Steroids, Polyketides and their synthesis, Prostaglandins, Phenolics, Anthraquinones (3 Lectures) Importance and synthetic strategies to Aromatic a-Amino Acids, Lignans, Coumarins, Flavonoids and Antibiotics (5 Lectures) Alkaloids: piperidines, indolizidines, quinolizidines, carbazoles, toxins (nicotine, lupinines, strychnine etc.), drugs (cocaine, opiates, quinine, vincristine etc.) (5 Lectures) |
| References |
|---|
| Suggested Books:
(1) Heterocyclic chemistry - J.A. Joule, K. Mills & G.F. Smith. (2) Comprehensive Heterocyclic Chemistry - A. R. Katritzky and C. W. Rees 69 (3) Heterocyclic Chemistry - T. L. Gilchrist. (4) The Essence of Heterocyclic Chemistry, New Age International Publications, 2013. (5) Heterocycles in Natural Product Synthesis by K. C. Majumder and Shital K. Chattopadhyay (6) Molecules that Changed the World by K. C. Nicolaou and Tamsyn Montagnon (WILEY-VCH) (7) The Way of Synthesis by Thomas Hudlicky and Josephine W. Reed (WILEY-VCH) (8) Protecting Group Free Organic Synthesis: Improving Economy and Efficiency by Rodney A. Fernandes (WILEY-VCH) (9) Classics in Total Synthesis: Targets, Strategies, Methods by K. C. Nicolaou and E. J. Sorensen (WILEY-VCH) (10) Classics in Total Synthesis II: More Targets, Strategies, Methods by K. C. Nicolaou and S. A. Snyder (WILEY-VCH) (11) Classics in Total Synthesis III: Further Targets, Strategies, Methods by Jason S. Chen and K. C. Nicolaou (WILEY-VCH) |
Course Credit Options
| Sl. No. | Programme | Semester No | Course Choice |
|---|---|---|---|
| 1 | IP | 2 | Not Allowed |
| 2 | IP | 4 | Not Allowed |
| 3 | MP | 2 | Not Allowed |
| 4 | MP | 4 | Elective |
| 5 | MR | 2 | Not Allowed |
| 6 | MR | 4 | Not Allowed |
| 7 | MS | 10 | Not Allowed |
| 8 | MS | 4 | Not Allowed |
| 9 | MS | 6 | Not Allowed |
| 10 | MS | 8 | Elective |
| 11 | RS | 1 | Elective |
| 12 | RS | 2 | Elective |