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On the reaction of isothiosemicarbazides with heterocumulenes. Part I
Author(s) -
Ernst Steffen,
Schulze Klaus
Publication year - 1996
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.5570330135
Subject(s) - chemistry , imine , isothiocyanate , yield (engineering) , thiazoline , medicinal chemistry , cyanate , organic chemistry , catalysis , materials science , metallurgy
Isothiosemicarbazides 2 react with acyl isothiocyanates under addition‐cyclization to yield 1,3,4‐thiadiazoline‐2‐imines 3 as well as the isomeric 2‐amino‐substituted 1,3,4‐thiadiazolium‐5‐acylaminides 3′ . In a similar manner the 2‐hydrazino‐substituted 1,3‐thiazoline 4 adds ethoxycarbonyl isothiocyanate to give the thiosemicarbazide 5 , which undergoes a rearrangement to the 1,3,4‐thiadiazoline‐2‐imine 5′. The [2+2] cycloreversion of 3d involving ethoxycarbonyl iso(thio)cyanate and the thermal induced Dimroth rearrangement of 3′f and h are also discussed.