Synthesis of 1, 2, 6-thiadiazine 1, 1-dioxides via isoxazolylsulfamides

HA Albrecht, JF Blount, FM Konzelmann…

Index: Albrecht,H.A. et al. Journal of Organic Chemistry, 1979 , vol. 44, p. 4191 - 4194

Full Text: HTML

Citation Number: 10

Abstract

7a, R'= H; R2= Me; R3= H b, R'= Me; R2= H; R3= Et c, R'= Me; Itz= H; R3= 4-MeOC, H4 gave 6a in rather poor yield due to formation of 2-cyanopropanamide as a major byproduct. Being unsubstituted in the 3-position, 5a readily underwent ring opening to the nitrile and proved quite vulnerable to acid. The stability of the isoxazole nucleus was markedly enhanced by incorporation into the sulfamide 6a. Hydrogenation of 6a in DMF over Raney nickel ...