Pharmaceutical organic chemistry-III

Teacher

KAMINI SETHY

Category

Core Courses

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Course Objectives

The course objective is to impart knowledge on stereo-chemical aspects of organic compounds and organic reactions, important named reactions, chemistry of important hetero cyclic compounds. It also emphasizes on medicinal and other uses of organic heterocyclic compounds.

Learning outcomes

Upon completion of the course students will be able to understand the importance and role of stereochemistry in drugs and pharmaceuticls for their activity. importance of reactions of chiral molecules and method of preparation, properties and role of different heterocycles in organic compounds with their reactivity and aromaticity

Syllabus

Module I

Stereo isomerism
Optical isomerism –
Optical activity, enantiomerism, diastereoisomerism, meso compounds
Elements of symmetry, chiral and achiral molecules
DL system of nomenclature of optical isomers, sequence rules, RS system of
nomenclature of optical isomers
Reactions of chiral molecules
Racemic modification and resolution of racemic mixture.
Asymmetric synthesis: partial and absolute

Module-II

Geometrical isomerism
Nomenclature of geometrical isomers (Cis Trans, EZ, Syn Anti systems)
Methods of determination of configuration of geometrical isomers.
Conformational isomerism in Ethane, n-Butane and Cyclohexane.
Stereo isomerism in biphenyl compounds (Atropisomerism) and conditions for optical
activity.
Stereospecific and stereoselective reactions

Module-III

Heterocyclic compounds:
Nomenclature and classification
Synthesis, reactions and medicinal uses of following compounds/derivatives Pyrrole,
Furan, and Thiophene
Relative aromaticity and reactivity of Pyrrole, Furan and Thiophene

Module-IV

Synthesis, reactions and medicinal uses of following compounds/derivatives Pyrazole,
Imidazole, Oxazole and Thiazole. Pyridine, Quinoline, Isoquinoline, Acridine and
Indole. Basicity of pyridine, Synthesis and medicinal uses of Pyrimidine, Purine,
azepines and their derivatives

Module-V

Reactions of synthetic importance
Metal hydride reduction (NaBH4 and LiAlH4), Clemmensen reduction, Birch
reduction, Wolff Kishner reduction.
Oppenauer-oxidation and Dakin reaction.
Beckmanns rearrangement and Schmidt rearrangement.
Claisen-Schmidt condensation

References

1. Organic chemistry by I.L. Finar, Volume-I & II.
2. A text book of organic chemistry – Arun Bahl, B.S. Bahl.
3. Heterocyclic Chemistry by Raj K. Bansal
4. Organic Chemistry byMorrison and Boyd

Session Plan

Session 1

Optical activity, enantiomerism, diastereoisomerism, meso compounds
Elements of symmetry, chiral and achiral molecules.Racemic modification and resolution of racemic mixture.

tereoisomerism,optical activity,resolution-converted

Session 2

 

sequence rules,

sequence rule

Session 3

 

DL system of nomenclature of optical isomers, RS system of
nomenclature of optical isomers

nomenclature stereoisomers

Session 4

Reactions of chiral molecules

reactions of chiral molecule

Session 5

Racemic modification and resolution of racemic mixture-given in study material session 1

Session 5

Asymmetric synthesis: partial and absolute

asymmetric synthesis

Session 6

Geometrical isomerism
Nomenclature of geometrical isomers (Cis Trans, EZ, Syn Anti systems)
Methods of determination of configuration of geometrical isomers.

nomenclaturevof geometrical isomers

Session 7

Conformational isomerism in Ethane, n-Butane and Cyclohexane

conformations of ethane ,n-butane& cyclohexane

Session 8

Stereo isomerism in biphenyl compounds (Atropisomerism)

Atropisomerism

Session 9

Stereospecific and stereoselective reactions

stereospecific and stereoselective reaction-

Session 10

Heterocyclic compounds,Nomenclature and classification

nomenclature of heterocycles

Session 11

Synthesis, reactions and medicinal uses of following compounds/derivatives Pyrrole,Furan, and Thiophene

heterocycles-pyrrole, furan and thiophene-

Session 12

Relative aromaticity and reactivity of Pyrrole, Furan and Thiophene

Session 13

Synthesis, reactions and medicinal uses of following compounds/derivatives Pyrazole,Imidazole, Oxazole and Thiazole

Pyrazole, Imidazole and Thiazole.

Session 14

Synthesis, reactions and medicinal uses Pyridine.Basicity of pyridine

pyridine-

Session 15

Quinoline, Isoquinoline, Acridine and Indole.

quinoline,isoquinoline,indole, acridine,phenothiazine

Session 16

Synthesis and medicinal uses of Pyrimidine, Purine

purine pyrimidine

Session 17

Metal hydride reduction (NaBH4 and LiAlH4), Clemmensen reduction, Birch
reduction, Wolff Kishner reduction.

named reactions

Session 18

Oppenauer-oxidation and Dakin reaction.

see course material session 17

Session 19

Beckmanns rearrangement and Schmidt rearrangement.Claisen-Schmidt condensation

see course material session 17

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