Pharmaceutical organic chemistry-III

Teacher

KAMINI SETHY

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Course Name: Pharmaceutical Organic Chemistry-III

Code(Credit): BPHT2201(4-0-0)

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

stereoisomerism,optical activity,resolution

Session 2

Elements of symmetry, chiral and achiral molecules

chirality and elements of symmetry

session 3

Racemic modification and resolution of racemic mixture.

resolution of racemic mixture

Session 4

sequence rules,

sequence rule

Session 5

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

nomenclature stereoisomers

Session 6

Reactions of chiral molecules

reactions of chiral molecule

Session 7

Asymmetric synthesis: partial and absolute

asymmetric synthesis

Session 8

Geometrical isomerism
Nomenclature of geometrical isomers (Cis Trans, EZ, Syn Anti systems)

nomenclaturevof geometrical isomers

Session 9

Methods of determination of configuration of geometrical isomers

Determination of configuration of geometrical isomers

Session 10

Conformational isomerism in Ethane, n-butane

conformations of ethane,n-butane

Session 11

Conformational isomerism in  Cyclohexane

conformations of cyclohexane

Session 12

Stereo isomerism in biphenyl compounds (Atropisomerism)

Atropisomerism

Session 13

Stereospecific and stereoselective reactions

stereospecific and stereoselective reaction-

Session 14

Heterocyclic compounds,Nomenclature and classification

nomenclature of heterocycles

Session 15

Synthesis, reactions and medicinal uses of  Pyrrole

heterocycles-pyrrole, furan and thiophene-

Session 16

Synthesis, reactions and medicinal uses of  Furan

heterocycles-pyrrole, furan and thiophene-

Session 17

Synthesis, reactions and medicinal uses of  Thiophene

heterocycles-pyrrole, furan and thiophene-

Session 18

Relative aromaticity and reactivity of Pyrrole, Furan and Thiophene

relative aromaticity pyrrole,furan,thiophene

Session 19

Synthesis, reactions and medicinal uses of  Pyrazole

pyrazole

Session 20

Synthesis, reactions and medicinal uses of Imidazole

imidazole

Session 21

Synthesis, reactions and medicinal uses of Oxazole

Oxazole

Session 22

Synthesis, reactions and medicinal uses of  Thiazole

Thiazole

Session 23

Synthesis of pyridine

pyridine-

Session 24

Reactions and medicinal uses Pyridine.Basicity of pyridine

pyridine-

Session 25

Synthesis, chemical properties and uses of Quinoline

quinoline,isoquinoline,indole, acridine,phenothiazine

Session 26

Synthesis, chemical properties and uses of Isoquinoline

quinoline,isoquinoline,indole, acridine,phenothiazine

Session 27

Synthesis, chemical properties and uses of Indole

quinoline,isoquinoline,indole, acridine,phenothiazine

Session 28

Synthesis, chemical properties and uses of Acridine

quinoline,isoquinoline,indole, acridine,phenothiazine

Session 29

Synthesis, chemical properties and uses of Phenothiazine

quinoline,isoquinoline,indole, acridine,phenothiazine

Session 30

Synthesis and medicinal uses of Pyrimidine

purine pyrimidine

Session 31

Synthesis and medicinal uses of  Purine

purine pyrimidine

Session 32

Metal hydride reduction (NaBH4 and LiAlH4)

named reactions

Session 33

Clemmensen reduction

named reactions

Session 34

Birch reduction, Wolff Kishner reduction.

named reactions

Session 35

Oppenauer-oxidation and Dakin reaction.

Oppenauer oxidation and Dakin reaction

Session 36

Beckmann's rearrangement

Beckmann's rearrangement

Session 37

Schmidt rearrangement.

Schmidt rearrangement

Session 38

Claisen-Schmidt condensation

Claisen-Schmidt Condensation

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