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Heterocyclic Chemistry
This course will enable the students to
gain the knowledge about the structures, syntheses, reactions, and properties of the major classes of heterocyclic compounds.
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Course |
Learning outcome (at course level) |
Learning and Teaching Strategies |
Assessment Strategies |
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Course Code |
Course Title |
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24CHY423 B |
Heterocyclic Chemistry (Theory) |
CO167: Explain the systematic nomenclature and general behavior of aromatic heterocyclic compounds. CO168: Discuss conformational analysis of heterocycles along with the associated changes in small ring heterocycles due to strain involved. CO169: Describe the synthesis and mechanisms of reactions involving small ring heterocycles. CO170: Appraise the synthesis and reactivity of the prescribed benzo-fused five-membered heterocycles & meso ionic compounds. CO171:Discuss the reactions and properties of six membered heterocycles having one or more hetero atoms. CO172: Contribute effectively in course-specific interaction. |
Approach in teaching: Interactive lectures, tutorials, group discussions and e-learning.
Learning activities for the students: Peer learning, e- learning, problem solving through tutorials and group discussions.
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Written examinations, Assignments, Quiz
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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.
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.
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.
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.
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.
- 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.
- 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:
- https://nptel.ac.in/courses/104105034
- http://www.chem.gla.ac.uk/staff/stephenc/teaching/HeterocycleLectures2011_2C12.pdf
- https://baranlab.org/wp-content/uploads/2018/09/Mesoionic-Compounds.pdf (Mesoionic Compounds)
