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Stereoselective synthesis of 2,3-disubstituted indoline, pyrrolidine and cyclic ether-fused 1,2-dihydroquinoline derivatives using alkyne iminium ion cyclization of vinylogous carbamates: switch of regioselectivity using an internal hydroxy group as a nucleophile.

Authors
  • Gharpure, Santosh J1
  • Prasath, V
  • Kumar, Vinod
  • 1 Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India. [email protected] , (India)
Type
Published Article
Journal
Chemical Communications
Publisher
The Royal Society of Chemistry
Publication Date
Sep 14, 2015
Volume
51
Issue
71
Pages
13623–13626
Identifiers
DOI: 10.1039/c5cc05292k
PMID: 26226402
Source
Medline
Language
English
License
Unknown

Abstract

An intramolecular, alkyne iminium ion cyclization of vinylogous carbamates derived from o-alkynyl anilines and N-protected homopropargyl amines is developed for the stereoselective construction of trans-2,3-disubstituted indolines and pyrrolidine derivatives, respectively. The regioselectivity of the alkyne iminium ion cyclization could be switched using a hydroxy group as an internal nucleophile resulting in cyclic ether-fused 1,2-dihydroquinolines. The entire process of nitrogen heterocycle formation can also be carried out in a 'one-pot' manner starting from o-iodo aniline derivatives.

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