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Reaction of 1‐acylthiosemicarbazides with ethenetetracarbonitrile
Author(s) -
Hassan Alaa A.,
Mourad AboulFetouh E.,
AbouZied Ashraf H.
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440532
Subject(s) - chemistry , hydrazide , oxadiazole , medicinal chemistry , stereochemistry , organic chemistry
1‐Acylthiosemicarbazides 9a‐d reacted with ethenetetracarbonitrile (TCNE, 2 ) in ethyl acetate with formation of N ′‐(4‐amino‐5,6‐dicyano‐2 H ‐1,3‐thiazin‐2‐ylidene) substituted hydrazide 10a‐d , N ′‐(5‐amino‐3,4‐dicyano‐2 H ‐pyrrol‐2‐ylidene)‐2‐substituted hydrazide 11a‐d and 2‐substituted imidazo[2,1‐ b ][1,3,4]‐oxadiazole‐5,6‐dicarbonitrile 12a‐d . Rationales for the conversions observed are presented.