Heteroannulation through copper catalysis: a novel cyclization leading to a highly regio- and stereoselective synthesis of 2-substituted benzothiazolines.

Org Lett

Department of Organic Chemistry, Indian Association for the Cultivation of Science, Calcutta.

Published: February 2000

AI Article Synopsis

  • The compound 3-(2-Aminophenylthio)prop-1-yne reacts with various aryl iodides using palladium-copper catalysis to produce disubstituted alkynes.
  • After undergoing tosylation, these alkynes enter a unique cyclization process mediated by copper, resulting in the formation of 2-substituted benzothiazolines.
  • Interestingly, the anticipated product of 3-(arylidine)-2,3-dihydrobenzothiazines was not achieved in this process.

Article Abstract

[reaction: see text] 3-(2-Aminophenylthio)prop-1-yne 8 reacted with aryl iodides 9-18 under palladium-copper catalysis leading to the disubstituted alkynes 19-28 which after tosylation underwent a novel cyclization under copper catalysis to 2-substituted benzothiazolines 29-38. The expected 3-(arylidine)-2,3-dihydrobenzothiazines were not obtained.

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Source
http://dx.doi.org/10.1021/ol990165gDOI Listing

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