American Chemical Society
ol070107s_si_002.pdf (1.66 MB)

Base-Mediated Reaction of the Bestmann−Ohira Reagent with Nitroalkenes for the Regioselective Synthesis of Phosphonylpyrazoles

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journal contribution
posted on 2007-03-15, 00:00 authored by R. Muruganantham, Shaikh M. Mobin, Irishi N. N. Namboothiri
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 α-bromonitroalkenes. The methodology works for the synthesis of phosphonylpyrazoles fused to other carbo- and heterocycles as well.