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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

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Title 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
 
Creator GHARPURE, SJ
PRASATH, V
KUMAR, V
 
Subject RADICAL CYCLIZATION
DIASTEREOSELECTIVE SYNTHESIS
BETA-AMINOACRYLATES
CONSTRUCTION
CARBONATES
ACID
ALKALOIDS
ENAMINONES
YLIDES
 
Description 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.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2016-01-15T07:02:15Z
2016-01-15T07:02:15Z
2015
 
Type Article
 
Identifier CHEMICAL COMMUNICATIONS, 51(71)13623-13626
1359-7345
1364-548X
http://dx.doi.org/10.1039/c5cc05292k
http://dspace.library.iitb.ac.in/jspui/handle/100/17999
 
Language en