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Five-Membered Heterocycles with One Heteroatom

  • Chapter
Heterocyclic Chemistry

Abstract

Five-membered aromatic heterocycles with one heteroatom; pyrrole 2, furan 3 and thiophene 4, are considered to be derived from cyclopentadienyl anion 1 by replacing CH group by NH, O and S, respectively (scheme-1). These five-membered heterocycles are, therefore, expected to possess characteristics of conjugated dienes and of acyclic amines, ethers and sulfides accordingly. In addition to their tendency to undergo addition reactions, these heterocycles also have characteristics associated with aromaticity; (i) electrophilic substitution reactions, (ii) resonance stabilization and (iii) aromatic sextet involving the lone pair on the heteroatom.

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  1. Department of Chemistry, University of Rajasthan, 302004, Jaipur, India

    Prof. Radha Raman Gupta, Dr. Mahendra Kumar & Dr. Vandana Gupta

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Gupta, R.R., Kumar, M., Gupta, V. (1999). Five-Membered Heterocycles with One Heteroatom. In: Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-07757-3_2

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