84662-06-6Relevant articles and documents
Cycloaddition Reactions of Heterocumulenes, XXVI. Cycloadducts from Aryl Isothiocyanates and 2,2-Disubstituted Enamines
Schaumann, Ernst,Baeuch, Hans-Guenther,Sieveking, Stefan,Adiwidjaja, Gunadi
, p. 55 - 65 (2007/10/02)
Aryl isothiocyanates 1 react with enamines 2 to give two types of 2:1 cycloadducts.Below 50 deg C, 1a - g and 2 give rise to 6-imino-1,3-thiazine-2-thiones 5, the constitutions of which are proved by an X-ray analysis of 5c.Above 50 deg C or starting from 4-nitrophenyl isothiocyanate (1h), 2,4-dithiouracils 6 are formed. 1:1 cycloadducts of the reactants are detected spectroscopically; on workup, they hydrolyze to give 2-formylthiopropionanilides 9.