Synthesis of the symmetrical 3,5-bis(difluoromethyl)-1,4-thiazine 1,1-dioxides

Add time:07/21/2019    Source:sciencedirect.com

A convenient synthesis of the symmetrical bis(difluoromethyl)-1,4-thiazine 1,1-dioxides was carried out via heterocyclization of bis(2,2,3,3-tetrafluoropropyl)sulfone with ammonia and primary amines. The reaction with excess of ammonia leads to the formation of 3,5-bis(difluoromethyl)-4H-1,4-thiazine 1,1-dioxide. The result of the reaction with primary amines is determined by spatial nature of substituent at the nitrogen atom. 3,5-Bis(difluoromethyl)-4-propyl-4H-1,4-thiazine 1,1-dioxide and 3,5-bis(difluoromethyl)-4-(p-tolyl)-4H-1,4-thiazine 1,1-dioxide were prepared by the reactions of bis(2,2,3,3-tetrafluoropropyl)sulfone with n-propylamine and p-toluidine accordingly. The reaction of bis(2,2,3,3-tetrafluoropropyl)sulfone with tert-butylamine gives the 1,1′-sulfonylbis(N-(tert-butyl)-3,3-difluoroprop-1-en-2-amine).

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