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Transition-Metal-Catalyzed Selective Cyclization Strategy to 2-Substituted Benzofurans and Indoles en Route to the Oxa Analogues of Isocryptolepine

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Title Transition-Metal-Catalyzed Selective Cyclization Strategy to 2-Substituted Benzofurans and Indoles en Route to the Oxa Analogues of Isocryptolepine
 
Creator INDU, S
SUBRAMANIAN, P
KALIAPPAN, KP
 
Subject Synthetic methods
Cross-coupling
Cyclization
Domino reactions
ALIPHATIC NITRILES SYNTHESIS
PICTET-SPENGLER REACTION
ALKYL ARYL KETONES
INDOLOQUINOLINE ALKALOIDS
ELECTROPHILIC CYCLIZATION
SUBSTITUTED BENZOFURANS
EFFICIENT SYNTHESIS
O-IODOPHENOLS
PALLADIUM
CRYPTOSANGUINOLENTINE
 
Description A selective catalytic route to benzofurans and indoles from similar starting materials has been developed. A two-step protocol that involves a transition-metal-catalyzed domino Sonogashira coupling between 2-ethynylanilines and 2-iodophenols followed by selective O- and N-cyclizations afforded 2-(benzofuran-2-yl)anilines and 2-(indol-2-yl)phenols, respectively. The 2-(benzofuran-2-yl) anilines were further utilized in a Lewis acid catalyzed Pictet-Spengler-type cyclization to prepare the oxa analogues of isocryptolepine.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-12-28T11:22:54Z
2014-12-28T11:22:54Z
2014
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (32)7193-7202
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201402869
http://dspace.library.iitb.ac.in/jspui/handle/100/16348
 
Language English