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Dicyanomethylene compounds and heterocyclization of acylthiosemicarbazides

✍ Scribed by Alaa A. Hassan; Aboul-Fetouh E. Mourad; Ashraf H. Abou-Zeid

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
351 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

(1,3‐Dioxo‐2,3‐dihydro‐1__H__‐inden‐2‐ylidene)propanedinitrile (1, in ethyl acetate solution), 3‐(dicyano‐methylene)‐2‐indolone (2, in ethanol/piperidine solution) and 7,7′,8,8′‐tetracyanoquinodimethane (3, in pyridine solution) act on substituted acylthiosemicarbazides 4a‐d, forming the derivatives of oxoindeno‐pyrrolylidenehydrazide (5a‐d and 7a‐d), thiazoloindolylidenehydrazide (12a‐d), pyrroloindolylidene‐hydrazide (13a‐d) and spiro[pyrrolylidene‐4,1′(cyclohexa‐2′,5′‐dienylidene)]propanedinitrile (18a‐d). Rationales for these conversiones involving the nucleophilic addition on dicyanomethylene carbon atom are presented.

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