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Base-mediated reaction of the Bestmann-Ohira Reagent with nitroalkenes for the regioselective synthesis of phosphonylpyrazoles

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Title Base-mediated reaction of the Bestmann-Ohira Reagent with nitroalkenes for the regioselective synthesis of phosphonylpyrazoles
 
Creator MURUGANANTHAM, RAJENDRAN
SHAIKH, MOBIN M
NAMBOOTHIRI, IRISHI NN
 
Subject phosphonyl pyrazoles
bestmann-ohira reagent
nitroalkenes
 
Description 1,3-Dipolar cycloaddition of the anion of diethyl 1-diazomethylphosphonate, generated in situ from diethyl 1-diazo-2- oxopropylphosphonate (Bestmann-Ohira reagent), with conjugated nitroalkenes provides regioisomerically pure phosphonylpyrazoles in moderate to good yield. These pyrazoles are formed in one pot via spontaneous elimination of the nitro group. However, nitropyrazoles could be synthesized by the same strategy using alpha-bromonitroalkenes. The methodology works for the synthesis of phosphonylpyrazoles fused to other carbo- and
heterocycles as well.
 
Publisher American Chemical Society
 
Date 2009-02-25T12:24:08Z
2011-11-25T17:53:33Z
2011-12-26T13:06:14Z
2011-12-27T05:54:03Z
2009-02-25T12:24:08Z
2011-11-25T17:53:33Z
2011-12-26T13:06:14Z
2011-12-27T05:54:03Z
2006
 
Type Article
 
Identifier Org. Lett. 9, 1125-28
0022-3263
http://dx.doi.org/10.1021/ol070107s
http://hdl.handle.net/10054/783
http://dspace.library.iitb.ac.in/xmlui/handle/10054/783
 
Language en