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Tandem Michael addition/imino-nitrile cyclization synthesis of 2-amino-6-(1-aryl-5-methyl-1H-1,2,3-triazol-4yl)-4-phenylpyridine-3-carbonitrile

✍ Scribed by Heng-Shan Dong; Hui-Cheng Wang; Zhong-Lian Gao; Rong-Shan Li; Fu-Hong Cui


Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
776 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

magnified image Several 2–amino‐6‐(1‐aryl‐5‐methyl‐1__H__‐1,2,3‐triazol‐4‐yl)‐4‐phenylpyridine‐3‐carbonitrile have been synthesized by Tandem Michael addition/imino‐nitrile cyclization and the structures of these compounds were established by MS, IR, CHN, and ^1^H NMR spectral data. The crystal structure of 2‐amino‐6‐[1‐(4‐methoxyphenyl)‐5‐methyl‐1__H__‐1,2,3‐triazol‐4‐yl]‐4‐phenylpyridine‐3‐carbonitrile was established by X‐ray diffraction. J. Heterocyclic Chem., (2010).


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## Abstract 2‐Amino‐6‐(3‐methyl‐5‐oxo‐1‐phenyl‐2‐pyrazolin‐4‐yl)‐4‐phenylpyridine‐3‐carbonitrile (1) obtained by the reaction of 4‐(1‐iminoethyl)‐3‐methyl‐1‐phenyl‐2‐pyrazolin‐5‐one with benzylidenemalononitrile, was reacted with triethyl orthoformate followed by hydrazine hydrate, acetic anhydride

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The Schiff bases 3a-h obtained from 4-amino-1,2,4-triazol-3-ones 1a-h when subjected to Japp-Klingemann reaction yielded the corresponding 3-{2-[(2-aryl-5-methyl-3H-[1,2,4]-triazol-3-one-4-yl)]-iminophenyl}-pentane-2,4-diones 4 a-h. These diones on cyclisation with N 2 H 4 yielded the title compound