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An efficient two-step synthesis of novel thiazolo[2,3-b]pyrazolo[3,4-f][1,3,5]triazepines

✍ Scribed by Braulio Insuasty; Alexis Tigreros; Henry Martínez; Jairo Quiroga; Rodrigo Abonia; Alexander Gutierrez; Manuel Nogueras; Justo Cobo

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
157 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

In an attempt to carry out a straightforward synthesis of thiazolopyrazolodiazepines from the reaction of 4,5‐diamino‐3‐methyl‐1‐phenylpyrazole 1 with arylidene derivatives of rhodanine 2, the unplanned (Z)**‐**2′‐[(5‐amino‐3‐methyl‐1‐phenylpyrazol‐4‐yl)imino]‐5‐arylidenethiazolidin‐4‐ones 4 were obtained as unique products. Nevertheless, the treatment of these compounds with aliphatic aldehydes in dimethylformamide provided the novel thiazolo[2,3‐b]pyrazolo[3,4‐f][1,3,5]triazepines 5 and 6 in good to excellent yields. All the structures of the obtained compounds were assigned on the basis of IR, 1D and 2D NMR measurements, mass spectrometry, and microanalysis. J. Heterocyclic Chem., (2009).

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