Synthesis of novel thiazole and pyrrolothiadiazine derivatives from aldehyde thiosemicarbazones

Abstract

Substituted thiosemicarbazones 7a-e reacted with ethenetetracarbonitrile (TCNE) in ethyl acetate with formation

Reactivity of 2-substituted hydrazinecarbothioamides towards tetracyanoethylene and convenient synthesis of (5-amino-2-diazenylthiazolylmethylene)malononitrile derivatives

“…19 5-Amino-3-(substituted benzylidenamino)-2-phenylimino-2,3-dihydrothiazole-4-carbonitrile is one of the products which have been isolated from the reaction of aldehyde thiosemicarbazones with tetracyanoethylene (TCNE). 20 Mesoionic 1,2,4-triazolium-3-thiolate derivatives were synthesized from the reaction of Nsubstituted 2-phenylhydrazinecarbothioamides with TCNE. 21 Herein, we report our investigation on the reaction of 2-substituted hydrazinecarbothioamides 1a-e with TCNE 2 (Fig.…”

Novel Synthesis of 1,3‐Thiazine and Pyrimidinethione Derivatives from (1‐Aryl ethylidene)hydrazinecarbothioamides and Tetracyanoethylene

“…It has been reported that substituted thiosemicarbazones 1a , 1b , 1c , 1d , 1e reacted with TCNE ( 2 ) in ethyl acetate with the formation of products 3 to 5 (Scheme ) .…”

“…Also, according to the formation of 3 , 4 , 5 , both the thioxosulfur and azomethine groups had taken part in heterocyclization .…”

Synthesis of novel spiro(indolone‐3,2′‐[1,3,4]thiadiazol)‐2‐ones and evaluation of their antidepressant and anticonvulsant activities

“…A novel and a efficient procedure for the synthesis of thiosemicarbazones has been achieved via a multicomponents and catalyst‐free reaction of phenyl or p ‐ chlorophenyl isothiocyanate, hydrazine, and aldehydes or ketones [33]. Besides, thiosemicarbazones are versatile building blocks in the synthesis of densely substituted heterocycles [34–40]. It has been reported earlier that, isatin‐3‐thiosemicarbazones were cyclized to 5 H ‐ as ‐triazino[5,6‐ b ]indole‐3‐thiones in aqueous K 2 CO 3 [41–43].…”