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Pyrazoles and pyrazolo[4,3-e]pyrrolo[1,2-a]pyrazines II

✍ Scribed by Abdel-Rahman Farghaly; Hussein El-Kashef

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
138 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Synthesis of the title compounds was achieved using the anils 2a, 2b, 2c, 2d, 2e and 5a, 5b, 5c derived from the 4‐aminopyrazole 1 as starting materials. These compounds were allowed to react with mercaptoacetic acid in boiling dry benzene to afford the corresponding thiazolidinones and spiro‐thiazolidinones 3a, 3b, 3c, 3d, 3e and 6a, 6b, 6c, respectively. Pictet—Spengler reaction of the 4‐aminopyrazole hydrochloride 7 with aromatic aldehydes and cyclic ketones resulted in the formation of new pyrazolo[4,3‐e]pyrrolo[1,2‐a]pyrazines 8a, 8b, 8c, 8d, 8e and 9a, 9b, respectively. Other derivatives of pyrazolo pyrrolopyrazines 10 and 11 were obtained via the reaction of the amino derivative 1 with 1,1′‐carbonyldiimidazol and CS~2~, respectively. J. Heterocyclic Chem., (2011).

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## Abstract The synthesis of the title compounds was achieved using the key intermediate ethyl 4,6‐dimethyl‐3‐(pyrrol‐1‐yl)thieno[2,3‐__b__]pyridine‐2‐ carboxylate 2. This latter compound was obtained __via__ the interaction of the thienopyridine amino ester 1 with 2,5 dimethoxytetrahydrofuran in a