A CONVENIENT SYNTHESIS OF 2-(ALKYL(OR ARYL)SULFANYL)-2H-1,4-BENZOTHIAZIN-3(4H)-ONE DERIVATIVES

A convenient method for the preparation of 2-(alkyl(or aryl)sulfanyl)-2H-1,4-benzothiazin-3(4H)-one derivatives has been developed. Thus, methyl alkyl(2-{[(alkyl(or aryl)sulfanyl)methyl]sulfanyl}phenyl)carbamates, derived from commercially available 2-aminobenzenethiol by an easily operated three-st...

Full description

Saved in:
Bibliographic Details
Published inHeterocycles Vol. 99; no. 1; pp. 583 - 595
Main Authors Kobayashi, Kazuhiro, Kawano, Kazuki, Yamashita, Keita
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.04.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GREEN
Online AccessGet more information

Cover

More Information
Summary:A convenient method for the preparation of 2-(alkyl(or aryl)sulfanyl)-2H-1,4-benzothiazin-3(4H)-one derivatives has been developed. Thus, methyl alkyl(2-{[(alkyl(or aryl)sulfanyl)methyl]sulfanyl}phenyl)carbamates, derived from commercially available 2-aminobenzenethiol by an easily operated three-step sequence, are treated with two equivalents of lithium diisopropylamide (LDA) to generate carbanions stabilized by the adjacent two sulfur atoms, which immediately undergo 2H-1,4-benzothiazin-3(4H)-one ring formation by intramolecular attack onto the carbamate carbonyl accompanying elimination of methoxide. In addition, direct or stepwise introductions of alkyl groups to the 2-position are reported.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-18-S(F)1