Base-mediated reaction of the Bestmann− Ohira Reagent with nitroalkenes for the regioselective synthesis of phosphonylpyrazoles
R Muruganantham, SM Mobin, INN Namboothiri - Organic Letters, 2007 - ACS Publications
R Muruganantham, SM Mobin, INN Namboothiri
Organic Letters, 2007•ACS Publications1, 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 …
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 …
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.
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