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Regioselective Synthesis of Sulfonylpyrazoles via Base Mediated Reaction of Diazosulfones with Nitroalkenes and a Facile Entry into Withasomnine

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Title Regioselective Synthesis of Sulfonylpyrazoles via Base Mediated Reaction of Diazosulfones with Nitroalkenes and a Facile Entry into Withasomnine
 
Creator KUMAR, R
NAMBOOTHIRI, INN
 
Subject BESTMANN-OHIRA REAGENT
BAYLIS-HILLMAN ADDUCTS
ONE-STEP SYNTHESIS
VINYL SULFONES
INTRAMOLECULAR CYCLOPROPANATION
ASYMMETRIC CATALYSIS
RADICAL CYCLIZATION
BIOLOGICAL-ACTIVITY
PYRAZOLE ALKALOIDS
CHEMISTRY
 
Description A base mediated reaction of alpha-diazo-beta-ketosulfone with nitroalkenes affords sulfonylpyrazoles as single regioisomers in excellent yield in a one-pot room temperature reaction. Aryl, heteroaryl, styrenyl, alkyl, hydroxymethyl, and hydrazinyl groups could be introduced on the pyrazole ring by the appropriate choice of nitroalkenes. Synthesis of sulfonylpyrazole fused to other heterocycles and application of the methodology to an expedient synthesis of a pyrazole alkaloid, Withasomnine, are also reported.
 
Publisher AMER CHEMICAL SOC
 
Date 2012-06-26T09:08:48Z
2012-06-26T09:08:48Z
2011
 
Type Article
 
Identifier ORGANIC LETTERS,13(15)4016-4019
1523-7060
http://dx.doi.org/10.1021/ol2015341
http://dspace.library.iitb.ac.in/jspui/handle/100/14262
 
Language English