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Semester III · PCI syllabus 2026
Heterocyclic Compounds and Stereochemistry
BP305T
3 credits
Theory
Coming soon
Unit 1: Chemistry of Carboxylic acids, Phenols, Amines and Polynuclear
- Aromatic hydrocarbons 1. Aliphatic and aromatic carboxylic acids
- Methods to prepare carboxylic acids (Oxidation of alcohols, carbonation of Grignard reagent, Kolbe-Schmidt reaction)
- Study of acidity of carboxylic acids and effect of substituents on acidity
- Study of chemical reactions of carboxylic acids [Mechanism of nucleophilic acyl substitution, Decarboxylation and Hell-Volhard- Zelinsky reaction]. Pharmaceutical applications of aromatic carboxylic acids (Benzoic acid, Salicylic acid, Acetyl Salicylic acid) 2. Aliphatic and aromatic amines
- Methods to prepare amines (Reduction of nitro compound, reduction of nitriles and Hofmann degradation of amides)
- Study of basicity of amines and effect of substituents on basicity
- Study of mechanism and synthetic applications of diazonium salts including Sandmeyer’s and azo-dye coupling reaction 3. Alcohols and Phenols
- Classification of alcohols, methods to prepare alcohols (oxymercuration - demercuration, reduction of carbonyl compounds)
- Acidity of alcohols and Phenols including effect of substituent on acidity
- Definition of phenols, method to prepare phenols by cumene process. Comparison of the acidity of phenol vs alcohol
- Study of mechanism of chemical reactions of phenols (Reimer- Tiemann reaction, halogenation and nitration of phenols). Pharmaceutical applications of alcohols and phenols (Glycerine, Thymol, Paracetamol) 4. Chemistry of polynuclear hydrocarbons Definition, and classification of polynuclear aromatic hydrocarbons, Study of synthesis (Haworth synthesis) and mechanism of electrophilic aromatic substitution reactions of naphthalene, phenanthrene and anthracene and medicinal uses of drugs containing Naphthalene (Propranolol, Naphazoline) and Phenanthrene (Morphine, Codeine)
Unit 2: Optical isomerism
- Definition of stereoisomerism and types of stereoisomerism with examples
- Definition with examples for optical activity, origin of chirality, elements of symmetry, chiral and achiral molecules, enantiomerism, diastereoisomerism and meso compounds
- Study of configuration including D & L system, sequence rules, R & S system. Medicinal importance of optical isomers with examples
Unit 3: Geometrical isomerism
- Nomenclature of geometrical isomers (Cis & Trans, E & Z, Syn & Anti system)
- Conformational isomerism and its analysis in ethane, butane and cyclohexane
- Stereo isomerism in biphenyl compounds (Atropisomerism) and conditions for optical activity in biphenyl compounds
Unit 4: Chemistry of five membered heterocycles
- IUPAC nomenclature and classification of heterocyclic compounds as per the Hansch- Widman system
- Relative aromaticity and reactivity of pyrrole, furan and thiophene
- Study of synthesis of pyrrole (Paal – Knorr synthesis), furan (Feist- Bénary reaction), thiophene (Hinsberg synthesis) and Mechanism of Electrophilic substitution reactions of pyrrole, furan and thiophene
- Medicinal uses of drugs containing pyrrole (Ethosuximide, procyclidine), furan (Furosemide, Nitrofurazone) and thiophene (Cephaloridine, Clopidogrel)
Unit 5: Chemistry of other heterocycles
- Study of nomenclature of fused heterocyclic compounds, synthesis for pyrazole (Knorr synthesis), imidazole (Debus-Radziszewski reaction), pyridine (The Hantzsch synthesis), quinoline (The Skraup synthesis) and Electrophilic aromatic substitution reactions of pyrazole and imidazole
- Chemical structures of Indole, pyrimidine, benzimidazole, purine, azepine, pyrazole, oxazole, Phenothiazine, benzotriazole, quinoxaline
- Basicity of imidazole, pyridine and quinolone
- Medicinal uses of any two drugs containing pyrazole (Sildenafil, Celecoxib), imidazole (Metronidazole, Pilocarpine), pyridine (Isoniazid, Chlorpheniramine), quinoline (Chloroquine, Ciprofloxacin), indole (Indomethacin, Reserpine), benzimidazole (Albendazole, Mebendazole) pyrimidine (Fluorouracil, Sulphadiazine), purine (Mercaptopurine, Thioguanine), azepine (Diazepam, Loxapine) heterocycles
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