Journal of Organic Chemistry p. 2757 - 2760 (1982)
Update date:2022-08-02
Topics:
Sasaki, Tadashi
Ito, Eikoh
Shimizu, Ikuo
s-Triazole-fused heterocycles have been synthesized by an intramolecular transformation of some 1,3,4-oxadiazole ketones with ammonia or hydrazine.The α-<(1,3,4-oxadiazol-2-yl)thio> ketone 2m gave thiazolo<2,3-c>-s-triazole (4m), accompanied by a small amount of the hydrazide 9m on treatment with ammonium acetate in acetic acid.Similar treatment of ketones 2a and 2b afforded only the hydrazides 9a and 9b, respectively.Ketones 2a-n reacted with hydrazine hydrate in acetic acid to give 7H-s-triazolo<3,4-b><1,3,4>thiadiazines 5a-n.However, ketones 2o-q, with substituents α to the carbonyl group, could not be converted to the corresponding fused-ring systems.Mechanisms for these transformations are proposed.
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Doi:10.1002/chem.19970030514
(1997)Doi:10.1016/S0031-9422(00)80538-5
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(1984)