HYDRAZINOLYSIS OF DIMETHYL 2-BROMO-1-(THIETAN-3-YL)- 1H-IMIDAZOLE-4,5-DICARBOXYLATES
Publication date: 2015
Abstract:
Alkylation of dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate with 2-chloromethylthiirane gave dimethyl 2-bromo-1-(thietan-3-yl)-1H-imidazole-4,5-dicarboxylate which was oxidized to dimethyl 2-bromo-1-(1-oxo-λ4-thietan-3-yl)- and 2-bromo-1-(1,1-dioxo-λ6-thietan-3-yl)-1H-imidazole-4,5-dicarboxylates. Reactions of the resulting thietanyl-substituted imidazoledicarboxylates with hydrazine afforded 2-bromo-1-(thietan-3-yl)-, 2-bromo-1-(1-oxo-λ4-thietan-3-yl)-, and 2-bromo-1-(1,1-dioxo-λ6-thietan-3-yl)-1H-imidazole-4,5-dicarbohydrazides and the corresponding 1-(thietanyl)-substituted 2-bromoimidazo[4,5-d]pyridazine-4,7(5H,6H)-diones.