HETEROCYCLIC CHEMISTRY

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

Course Objective(s) :

This course will enable the students to –
gain the knowledge about the structures, syntheses, reactions, and properties of the major classes of heterocyclic compounds.

Course Outcomes (COs):

Course Outcomes

Teaching Learning Strategies

Assessment Strategies

On completion of this course, the students will be able to-

CO134:learn and understand the specific properties and biological activities of some important heterocycles.

CO135:propose syntheses of heterocycles from the major classes and assign their names

CO136:describe mechanisms for reactions involving heterocycles as starting materials, intermediates and products.

CO137:compare the reactivity between the different heterocyclic structures and solve problems demonstrating an understanding of fundamental reactions of addition and nucleophilic reactions.

CO138:recognize and comment on  different synthetic strategies and methods for stereocontrol .

 
  • Interactive lectures
  • Tutorials
  • Group discussions
  • Use of models
  • Digital learning
  • Problem solving sessions
  • Assertion and Reasoning

 
  • Oral and written examinations
  • Assignments
  • Quiz

 

 
 


 

 

12.00
Unit I: 
Introduction and Nomenclature of Heterocycles

Replacement and systematic nomenclature (Hantzsch-Widman system) for monocyclic, fused and bridged heterocycles.
General chemical behavior 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 heterocycles-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 & Meso Ionic Heterocycles

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

 

Essential Readings: 
  • Heterocyclic Chemistry Vol. I & II, First Edition; R.R. Gupta and M. Kumar; Springer (India) Pvt. Ltd., 2011.
  • Heterocyclic Chemistry, Fifth Edition; J.A. Joule and K.Mills; Wiley-Blackwell, London, 2013.
  • Heterocyclic Chemistry, Third Edition; T.L. Gilchrist; Pearson Education,Delhi,2005.

 

References: 

SUGGESTED READINGS:

  • An Introduction to the Chemistry of Heterocyclic Compounds, Third Edition; R.M. Acheson; Wiley Eastern Ltd, New Delhi,1976.
  • Contemporary Heterocyclic Chemistry, First Edition, G.R. Newkome and W.W. Paudler, Wiley Interscience, 1982.

e-RESOURCES:

 

Academic Year: 
2023-2024
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