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Synthesis of functionalized and fused furans and pyrans from the Morita-Baylis-Hillman acetates of nitroalkenes

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Title Synthesis of functionalized and fused furans and pyrans from the Morita-Baylis-Hillman acetates of nitroalkenes
 
Creator NAIR, DK
MOBIN, SM
NAMBOOTHIRI, INN
 
Subject Furan
Pyran
Nitroalkene
Morita-Baylis-Hillman acetates
Cascade reaction
ANTIMICROBIAL ACTIVITY
KETONES
 
Description The Morita-Baylis-Hillman (MBH) acetates derived from nitroalkenes and ethyl glyoxylate have been transformed in one pot at room temperature to highly fused and functionalized furans and pyrans in good to excellent yield. The reaction involves a cascade Michael-oxa-Michael addition of beta-dicarbonyl compounds to the MBH acetates in the presence of an amine base such as DABCO. An unusual switching of selectivity in the oxa-Michael addition from 5-exo-trig to 6-endo-trig was observed when the beta-dicarbonyl compound was changed from acyclic or six-membered ring cyclic to five-membered ring cyclic system. (C) 2012 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-15T14:22:53Z
2014-10-15T14:22:53Z
2012
 
Type Article
 
Identifier TETRAHEDRON LETTERS, 53(26)3349-3352
http://dx.doi.org/10.1016/j.tetlet.2012.04.084
http://dspace.library.iitb.ac.in/jspui/handle/100/15092
 
Language en