Issue 0, 1981

Studies on heterocyclic chemistry. Part 24. Syntheses of the 4-arylisothiazol-3-yl O-thioesters utilising the S-thioester →O-thioester rearrangements of the 4-aryl-5-thioxo-3-isothiazolin-3-yl S-thioesters induced by acylation reagents, peracid, or N-bromosuccinimide

Abstract

A number of 4-arylisothiazol-3-yl O-thioesters have been prepared utilising the S-thioester O-thioester rearrangements of the 4-aryl-5-thioxo-3-isothiazolin-3-yl S-thioesters (1). Reactions of the isothiazolines with acylation reagents (e.g. acyl chloride or acid anhydride) in the presence of boron trifluoride afforded the 5-acylthio-4-arylisothiazol-3-yl O-thioesters (2), which were also prepared by the reactions of the thallium(I) 4-aryl-5-sulphidoisothiazol-3-yl O-thioesters (3) with acyl chloride. Reactions of the isothiazolines with m-chloroperbenzoic acid gave the 5,5′-dithiobis(4-arylisothiazol-3-yl O-thioesters)(5) and the 4-arylisothiazol-3-yl O-thioesters (6). The disulphides (5) were also accessible by the reaction of the isothiazolines with N-bromosuccinimide.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 1401-1406

Studies on heterocyclic chemistry. Part 24. Syntheses of the 4-arylisothiazol-3-yl O-thioesters utilising the S-thioester →O-thioester rearrangements of the 4-aryl-5-thioxo-3-isothiazolin-3-yl S-thioesters induced by acylation reagents, peracid, or N-bromosuccinimide

T. Nishiwaki, E. Kawamura, N. Abe and M. Iori, J. Chem. Soc., Perkin Trans. 1, 1981, 1401 DOI: 10.1039/P19810001401

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements