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Junjappa-Ila annulation: α-Oxoketene dithioacetal mediated synthesis of substituted benzotriazoles

✍ Scribed by Nitinkumar S. Shetty; Ravi S. Lamani; Shridhar I. Panchamukhi; Imtiyaz Ahmed M. Khazi

Publisher: Journal of Heterocyclic Chemistry
Year: 2009
Tongue: English
Weight: 67 KB
Volume: 46
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.85

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✦ Synopsis

Abstract

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2‐(1‐Benzyl‐1__H__–1,2,3‐triazole‐4‐yl)‐3‐methylsulfanyl‐5‐oxo‐5‐substituted‐pent‐2‐enenitrile 3a, 3b, 3c, 3d, 3e were obtained in good yields by condensation of (1‐benzyl‐1__H__‐1,2,3‐triazole‐4‐yl)acetonitrile 1 with various α‐oxoketene dithioacetals 2a, 2b, 2c, 2d, 2e in the presence of sodium hydride. The intermediates 3a, 3b, 3c, 3d, 3e underwent facile acid‐induced cyclization in the presence of PTSA to afford the corresponding benzotriazoles 4a, 4b, 4c, 4d, 4e in moderate yields. J. Heterocyclic Chem., (2009).

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