Abe Noritaka
Affiliate Master
Yamaguchi University
Studies on heterocyclic chemistry. part 21. Reaction of 3-mercapto-and 3-acylthio-3-isothiazoline-5-thiones : Ring transfomations, a baseinduced ring cleavage, and thiol-ester-thioxo-ester rearrangements
Journal of the Chemical Society. Perkin transactions 1 : organic and bio-organic chemistry Volume 1980
Page 2693-2699
published_at 1980
Title
Studies on heterocyclic chemistry. part 21. Reaction of 3-mercapto-and 3-acylthio-3-isothiazoline-5-thiones : Ring transfomations, a baseinduced ring cleavage, and thiol-ester-thioxo-ester rearrangements
Acylation of 4-aryl-3-mercapto-3-isothiazoline-5-thiones (1) with acid chloride in pyridine or alternatively with acid anhydride leads exclusively to 3-acylthio-4-aryl-3-isothiazoline-5-thiones (2). Reactions of (1) with reactive acetylenes afford 2-[aryl(thiocarbamoyl)methylene]-1,3-dithiole derivatives (3) whereas those of (2) with the acetylenes are accompanied by an S → N acyl migration giving N-benzoyl-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]arylethanethioamides (4). ^<13>C N.m.r. spectra and some chemical reactions of (3) and (4) are described. The ring-cleavage of (1) with base and the thiol-easter-thioxo-easter rearrangements of (2) induced by diazoalkane, alkyl iodide, or triethyloxonium tetrafluoroborate are also reported.
Languages
eng
Resource Type
journal article
Publishers
Royal Society of Chemistry
Date Issued
1980
File Version
Not Applicable (or Unknown)
Access Rights
metadata only access
Relations
[ISSN]0300-922X
[NCID]AA00695134
[isVersionOf]
[URI]http://www.rsc.org/Publishing/Journals/P1/
Schools
大学院医学系研究科（理学）