A convenient synthesis of 3,4-dihydro-2,2-dioxide 5-hydroxy-2,1-benzothiazine

3-methoxy-2-methyl-aniline 3 is converted to the benzothiazine-dioxide 1 in a 7-steps procedure: the key transformation being the cyclization of an ortho-functionnalized N-benzyl sulfonanilide. Compound 1 has been succesfully synthesized from 3-methoxy-2-methyl-aniline in 7 steps and 12% overall yie...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 18; pp. 2911 - 2912
Main Authors Blondet, Dominique, Pascal, Jean-Claude
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.05.1994
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Sulfur nitrogen heterocycle
Sulfonamide
Sultam
Cyclization
Bicyclic compound
Phenols
Aromatic compound
Aldehyde
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Summary:3-methoxy-2-methyl-aniline 3 is converted to the benzothiazine-dioxide 1 in a 7-steps procedure: the key transformation being the cyclization of an ortho-functionnalized N-benzyl sulfonanilide. Compound 1 has been succesfully synthesized from 3-methoxy-2-methyl-aniline in 7 steps and 12% overall yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)76657-3