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Stereoselective synthesis of C-fused pyranoindoles, pyranobenzofurans and pyranobenzothiophene scaffolds using oxa-Pictet-Spengler type reaction of vinylogous carbonates

DSpace at IIT Bombay

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Title Stereoselective synthesis of C-fused pyranoindoles, pyranobenzofurans and pyranobenzothiophene scaffolds using oxa-Pictet-Spengler type reaction of vinylogous carbonates
 
Creator GHARPURE, SJ
PRASATH, V
 
Subject PALLADIUM-CATALYZED REACTIONS
CYCLIZATION
ACID
DERIVATIVES
INDOLES
CONSTRUCTION
ALKYLATION
POLYMERASE
INHIBITORS
DISCOVERY
 
Description C-fused pyranoheterocycles can be readily assembled using an intramolecular oxa-Pictet-Spengler type reaction of vinylogous carbonates in a highly stereoselective manner. Required indole and benzofuran rings tethered to vinylogous carbonates are prepared by a tandem Sonogashira coupling-nucleopalladation reaction. The entire process can also be carried out in a 'one-pot' manner starting from homopropargyl alcohol. The C-fused pyranoindoles could be converted to spirooxindoles as well as to ring expanded products under oxidative conditions.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-12-28T12:12:09Z
2014-12-28T12:12:09Z
2014
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 12(37)7397-7409
1477-0520
1477-0539
http://dx.doi.org/10.1039/c4ob01387e
http://dspace.library.iitb.ac.in/jspui/handle/100/16460
 
Language English