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Heterocyclic Chemistry [1]

Paper Code: 
CHY 423 B
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

To learn about synthetic organic chemistry.

 

12.00
Unit I: 
Introduction and Nomenclature of Heterocycles

Replacement and systematic nomenclature (Hantzsch-Widman system) for monocyclic,     fused and bridged heterocycles.

General chemical behaviour of aromatic heterocycles, classification (structural type), criteria of aromaticity (bond lengths, ring current and chemical shifts in 1H NMR-spectra, empirical resonance energy, delocalization energy and Dewar resonance energy, diamagnetic susceptibility exaltations), heteroaromatic reactivity and tautomerism in aromatic heterocycles.

 

12.00
Unit II: 
Conformational Analysis of Non-aromatic Heterocycles

Strain-bond angle, torsional strains and their consequences in small ring heterocycles. Conformation of six-membered heterocycles with reference to molecular geometry, barrier to ring inversion, pyramidal inversion and 1,3-diaxial interaction, stereo-electronic effects:  anomeric and related effects, attractive interactions:  hydrogen bonding and intermolecular nucleophilic-electrophilic interactions.

 

12.00
Unit III: 
Small Ring Heterocycles

Three-membered and four membered heterocycles: synthesis and reactions of aziridines, oxiranes, thiiranes, azetidines, oxetanes and thietanes, five membered heterocycales: synthesis and reactions of different isomers of diazoles (pyrazoles, imidazoles), oxazoles, thiazoles, 1,2,4-triazole, oxadiazole, thiadiazole, 1,2,3,4-tetrazole.Porphyrins and applications.

 

12.00
Unit IV: 
Benzo-Fused Five-Membered Heterocycles and Meso Ionic

Synthesis and reactions including medicinal applications of benzopyrroles, benzofurans and benzothiophenes Meso-ionic heterocycles: classification, chemistry of some important meso-aionic heterocycles of type-A and B and their applications. Sydnones.

 

12.00
Unit V: 
Six Membered Heterocycles

With one heteroatom: synthesis and reactions of pyrilium salts and pyrones and their comparison with pyridinium and thiopyrylium salts and pyridones; synthesis and reactions of quinolizinium and benzopyrylium salts, coumarins and chromones.

With two or more heteroatoms: synthesis and reactions of diazines, triazines, tetrazines and thiazines. Some important macroheterocycles.

 

References: 
  1. Heterocyclic Chemistry Vol. I & II; First Edition; R.R. Gupta and M. Kumar; Springer (India) Pvt. Ltd., 2005.
  2. Heterocyclic Chemistry; Fourth Edition; J.A. Joule and K. Mills; Blackwell Science Ltd., London, 2000.
  3. Heterocyclic Chemistry; Third Edition; T. L. Gilchrist; Delhi: Pearson Education, 2008.
  4. An Introduction to the Chemistry of Heterocyclic Compounds; Second Edition; R.M. Acheson; New Delhi: Wiley Eastern Ltd, 1976.
  5. Contemporary Heterocyclic Chemistry; G.R. Newkome and W.W. Paudler; Wiley Interscience.

 

Academic Year: 
2018-2019 [2]

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Source URL: https://www.my-campus.iisuniv.ac.in/courses/subjects/heterocyclic-chemistry

Links:
[1] https://www.my-campus.iisuniv.ac.in/courses/subjects/heterocyclic-chemistry
[2] https://www.my-campus.iisuniv.ac.in/academic-year/2018-2019