On the reaction of thiazole-2,4-diamines with isothiocyanates - Preparation and transformation of 2,4-diaminothiazole-5-carbothioamides

Abstract

In the reaction of thiazole-2,4-diamines 8 with isothiocyanates 1, 2,4-diaminothiazole-5-carbothioamides 9, 10, 18, and 19 as well as thiazolo[4,5-d]pyrimidine-7(6H)-thiones 21 were formed. The carbothioamides 9, 10, and 18 were transformed by reaction with different types of monofunctional and bifunctional electrophiles into hitherto unknown acceptor-substituted 4,4′-([2,5′-bithiazole]-2′,4′-diyl)bis[morpholines] 24 and 29, the 2′,4′-bis(dialkylamino)[2,5′-bithiazol]-4-(5H)-ones 30, and the 4-substituted 2′,4′-bis(dialkylamino)-2,5′-bithiazoles 31. From 30 and 31 new 4-mono- or 4,5-disubstituted 2′,4′-bis(dialkylamino)-2,5′-bithiazoles 34, 35, 38, and 39 as well as 5-substituted 2′,4′- bis(dialkylamino)[2,5′-bithiazol]-4(5H)-ones 33, 36, and 37 were prepared.