Synthesis of 2 H-1, 2-Benzothiazine 1, 1-Dioxides via Heteroannulation Reactions of 2-Iodobenzenesulfonamide with Ketone Enolates under SRN1 Conditions §

WJ Layman, TD Greenwood, AL Downey…

Index: Layman Jr., William J.; Greenwood, Thomas D.; Downey, Aaron L.; Wolfe, James F. Journal of Organic Chemistry, 2005 , vol. 70, # 23 p. 9147 - 9155

Full Text: HTML

Citation Number: 28

Abstract

2-Iodobenzenesulfonamide (1a) underwent photostimulated SRN1 reactions in liquid NH3 with the potassium enolates derived from acetone, pinacolone, butanone, and 3-methyl-2- butanone to give fair to good yields of 2 H-1, 2-benzothiazine 1, 1-dioxides 2. Reductive dehalogenation of 1a was found to predominate in photoinduced reactions of 1a with 3- pentanone, 2-methyl-3-pentanone, and 2, 4-dimethyl-3-pentanone, the extent of reduction ...