1. Hetrocyclic Compounds
a) Definition, classification and nomenclature; Heterocyclic compounds containing 1,2 & 3 hetero-atoms and fused ring system
b) Detailed study of heterocycties including their reaction mechanism furan, nomenclature, molecular orbital picture, resonance hybrids. Preparation of furan and its derivatives: from mucic acid, decomposition of furfural, 1,4-diketo compounds, ethyl acetoacetate, and Fest-Benary Synthesis. Physical properties of furan. Reaction of furan: Addition reactions; hydrogenation, Diels-Alder reaction, 2,5-addition. Electrophilic substitution reactions: chlorination, nitration, sulfonation, mercuration, Friedel’s Craft alkylation and acylation, Gatterman koch reaction, Gomberg reaction. Formation of organomettalic compounds. Formation of pyrrole and thiophene. Ring opening reactions.
c) Pyrrole: nomenclature, molecular orbital picture, resonance hybrids. Preparation of pyrrole and its derivatives: from acetylene, ammonium mucate, succinimide, ethylacetoacetate; Paal Knorr Synthesis, Knorr pyrrole synthesis, Hantzsch synthesis. Physical properties of pyrrole. Reactions of pyrrole: Acidic and Basic character, Resemblance with aromatic amines and phenols. Addition reactions, Electrophilic substitution reactions; chlorination, nitration, sulfonation, Friedel’s Craft alkylation and acylation, Gatterman koch reaction, Reimer Tiemann reaction, Gomberg reaction., ring expansion and reduction.
d) Thiophene: nomenclature, molecular orbital picture, resonance hybrids. Preparation of thiophene and its derivatives; from acetylene, sodium succinate and n-butane. Physical properties of thiophene. Reaction of thiophene: addition reactions, electrophilic substitution reactions; chlorination, bromination, iodination, nitration, mercuration, Friedel’s Craft alkylation and acylation, chloromethylation. Formation of organomettalic compounds.
e) Pyridine: Molecular orbital picture, resonance hybrids. Preparation of pyridine and its derivatives; from acetylene, Hantzsch synthesis. Physical properties of pyridine. Reactions of pyridine; basic character, reduction, electrophilic substitution reactions; chlorination, nitration. Nucleophilic substitution reaction ; amination, alkylation etc.
This course includes introduction to heterocyclic chemistry specially Aromatic Heterocyclic compounds particularly five, six and seven-membered heterocyclic systems as well as fused heterocyclic systems. their synthesis, mechanism and properties is also discussed. their reactive positions in a ring is also discussed.
Course Learning Outcomes
this course is design to learn the importance of heterocyclic compounds because it has wide application in medicinal chemistry. the students get familiar with different types of Aromatic heterocyclic compounds. they learn to synthesize these molecules and familiar the class of compounds
Book Title : organic Chemistrychapter 44 Aromatic heterocycles
Author : Jonathan Clayden, Nick Greeves, and Stuart Warren
Edition : 1st
Publisher : Oxford university press