Reassignment of the Structures of Products Produced by Reactions of the Product Believed To Be 2-(1-Phenyl-2-Thiocyanatoethylidene)-malononitrile with Electrophiles 英文参考文献.docVIP
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Reassignment of the Structures of Products Produced by Reactions of the Product Believed To Be 2-(1-Phenyl-2-Thiocyanatoethylidene)-malononitrile with Electrophiles 英文参考文献
Molecules 2011, 16, 3456-3468; doi:10.3390/moleculeOPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Reassignment of the Structures of Products Produced by
Reactions of the Product Believed To Be 2-(1-Phenyl-2-
Thiocyanatoethylidene)-malononitrile with Electrophiles
Saleh Mohammed Al-Mousawi *, Moustafa Sherief Moustafa and Mohamed Hilmy Elnagdi
Department of Chemistry, Faculty of Science, University of Kuwait, Safat, 13060, P.O. Box 12613,
Kuwait
* Author to whom correspondence should be addressed; E-Mail: salehalmousawi@;
Tel.: +965 Fax: +965
Received: 1 April 2011; in revised form: 15 April 2011 / Accepted: 18 April 2011 /
Published: 26 April 2011
Abstract: The reactivity of the product believed to be 2-(1-phenyl-2-thiocyanato-
ethylidene)malononitrile toward a variety of electrophilic and nucleophilic reagents is
reported.
Keywords: 2-(1-phenyl-2-thiocyanatoethylidene)malononitrile; thiazole; diaminopyrazole;
pyrazolo[1,5-α] pyrimidinediamine
1. Introduction
Conflicting results have been reported for the structures of the products formed upon reaction of 2-
thiocyanatoethanones (1) with active methylene nitriles. In 1986, Abdelrazek et al [1] proposed that
reaction of 1a with malononitrile in refluxing ethanol in the presence of catalytic piperidine affords the
dicyanomethylidene adduct 2a. Recently a patent described the formation of the thiazole 3a from these
substrates under very similar conditions (Scheme 1) [2]. Abdelrazek subsequently [3] reported that 2a
could also be produced by reaction of the brominated dicyanomethylidene 4a with potassium
thiocyanate, although a detailed procedure for this transformation was not provided. This observation
served as evidence against the formation of 3a as the product of the reaction of 1a with malononitrile.
Thiazole 3a was also reported to form in the reaction between 1a and malononitrile in presence o
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