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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/3731

Title: Base-mediated reaction of the Bestmann-Ohira reagent with nitroalkenes for the regioselective synthesis of phosphonylpyrazoles
Authors: MURUGANANTHAM, R
MOBIN, SM
NAMBOOTHIRI, INN
Keywords: haloacetylated enol ethers
baylis-hillman adducts
1,3-dipolar cycloadditions
conjugated nitroalkenes
carbonyl-compounds
asymmetric-synthesis
facile synthesis
pyrazoles
diazoalkanes
alkynes
Issue Date: 2007
Publisher: AMER CHEMICAL SOC
Citation: ORGANIC LETTERS, 9(6), 1125-1128
Abstract: 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.
URI: http://dx.doi.org/10.1021/ol070107s
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3731
http://hdl.handle.net/10054/3731
ISSN: 1523-7060
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