Base-mediated reaction of the Bestmann-Ohira Reagent with nitroalkenes for the regioselective synthesis of phosphonylpyrazoles
DSpace at IIT Bombay
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Title |
Base-mediated reaction of the Bestmann-Ohira Reagent with nitroalkenes for the regioselective synthesis of phosphonylpyrazoles
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Creator |
MURUGANANTHAM, RAJENDRAN
SHAIKH, MOBIN M NAMBOOTHIRI, IRISHI NN |
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Subject |
phosphonyl pyrazoles
bestmann-ohira reagent nitroalkenes |
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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. |
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Publisher |
American Chemical Society
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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 |
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Type |
Article
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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 |
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Language |
en
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