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One-Pot Regioselective Synthesis of meta-Terphenyls via [3 + 3] Annulation of Nitroallylic Acetates with Alkylidenemalononitriles

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Title One-Pot Regioselective Synthesis of meta-Terphenyls via [3 + 3] Annulation of Nitroallylic Acetates with Alkylidenemalononitriles
 
Creator GOPI, E
NAMBOOTHIRI, INN
 
Subject MORITA-BAYLIS-HILLMAN
SOLVENT-FREE CONDITIONS
CONJUGATED NITROALKENES
NITROALLYLIC ACETATES
ADDITION-ELIMINATION
BENZENE-DERIVATIVES
FUNCTIONALIZED CYCLOPENTENES
KINETIC RESOLUTION
EFFICIENT
KETONES
 
Description A highly efficient one-pot method has been developed for the synthesis of meta-terphenyls via a regioselective [3 + 3] annulation-elimination sequence involving Morita-Baylis-Hillman (MBH) acetates of nitro-alkenes and alkylidenemalononitriles. The reaction takes place in a regioselective manner under mild conditions (Et3N, room temperature) to afford a wide variety of meta-terphenyls bearing aryl, heteroaryl and styrenyl groups. This novel [3 + 3] annulation takes advantage of the 1,3-bielectrophilic character of MBH acetates and 1,3-binucleophilic character of alkylidenemalononitriles and proceeds in a cascade fashion comprising an S(N)2' substitution, intramolecular 6-endo-trig Michael addition and double elimination. Representative synthetic transformations of the products, for instance, to meta-terphenyl derived isoindolinones have also been demonstrated.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-12-29T05:45:54Z
2014-12-29T05:45:54Z
2014
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 79(16)7468-7476
0022-3263
http://dx.doi.org/10.1021/jo501193h
http://dspace.library.iitb.ac.in/jspui/handle/100/17228
 
Language English