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 ...

Related Articles:

Novel N-dealkylation of N-alkyl sulfonamides and N, N-dialkyl sulfonamides with periodic acid catalyzed by chromium (III) acetate hydroxide

[Xu, Liang; Zhang, Suhong; Trudell, Mark L. Synlett, 2004 , # 11 p. 1901 - 1904]

Mild and general method for the synthesis of sulfonamides

[Garcia Ruano, Jose Luis; Parra, Alejandro; Yuste, Francisco; Mastranzo, Virginia M. Synthesis, 2008 , # 2 p. 311 - 319]

Simple and facile reduction of azides to amines: synthesis of DNA interactive pyrrolo [2, 1-c][1, 4] benzodiazepines

[Kamal, Ahmed; Reddy; Reddy, D.Rajasekhar Tetrahedron Letters, 2002 , vol. 43, # 37 p. 6629 - 6631]

Scandium Triflate as an Efficient and Recyclable Catalyst for the Deprotection of Tert??Butyl Aryl Sulfonamides

[Mahalingam; Wu, Xiongyu; Wan, Yiqian; Alterman, Mathias Synthetic Communications, 2005 , vol. 35, # 3 p. 417 - 425]

Novel N-dealkylation of N-alkyl sulfonamides and N, N-dialkyl sulfonamides with periodic acid catalyzed by chromium (III) acetate hydroxide

[Xu, Liang; Zhang, Suhong; Trudell, Mark L. Synlett, 2004 , # 11 p. 1901 - 1904]

More Articles...