Use of (Z)-β-(2-Fluorobenzenesulfonyl)vinylamines as Novel Synthons in the Synthesis of 1,4-Benzothiazine Derivatives

Gavin Chit Tsui; Yuttapong Singjunla; Mark Lautens

doi:10.1055/s-0031-1289741

Synthesis, Table of Contents

Synthesis 2012; 44(9): 1359-1364
DOI: 10.1055/s-0031-1289741

paper

Use of (Z)-β-(2-Fluorobenzenesulfonyl)vinylamines as Novel Synthons in the Synthesis of 1,4-Benzothiazine Derivatives

Gavin Chit Tsui

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: +1(416)9468185 Email: mlautens@chem.utoronto.ca

,

Yuttapong Singjunla

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: +1(416)9468185 Email: mlautens@chem.utoronto.ca

,

Mark Lautens*

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: +1(416)9468185 Email: mlautens@chem.utoronto.ca

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Abstract

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Abstract

A novel synthetic route for arylated 1,4-benzothiazine derivatives has been developed. This method utilizes a key intramolecular nucleophilic aromatic substitution step of the corresponding (Z)-β-(2-fluorobenzenesulfonyl)vinylamine intermediate to construct the benzothiazine ring. A wide range of aryl and heteroaryl substituent groups can be installed from commercial boronic acids. Both mono- and diarylated products have been synthesized in good yields and with good functional group tolerance.

Key words

heterocycles - rhodium - sulfone - nucleophilic aromatic substitution - cyclization

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References

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