Muruganantham, R. ; Mobin, Shaikh M. ; Namboothiri, Irishi N. N. (2007) Base-Mediated Reaction of the Bestmann−Ohira Reagent with Nitroalkenes for the Regioselective Synthesis of Phosphonylpyrazoles Organic Letters, 9 (6). pp. 1125-1128. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/ol070107s
Related URL: http://dx.doi.org/10.1021/ol070107s
Abstract
(Chemical Equation Presented) 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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 121585 |
| Deposited On: | 19 Jul 2021 10:47 |
| Last Modified: | 19 Jul 2021 10:47 |
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