Highly Selective Synthesis of Pyrazole and Spiropyrazoline Phosphonates via Base-Assisted Reaction of the Bestmann-Ohira Reagent with Enones
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Title |
Highly Selective Synthesis of Pyrazole and Spiropyrazoline Phosphonates via Base-Assisted Reaction of the Bestmann-Ohira Reagent with Enones
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Creator |
VERMA, D
MOBIN, S NAMBOOTHIRI, INN |
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Subject |
REGIOSELECTIVE SYNTHESIS
DERIVATIVES DIAZOMETHANE SPIRO-1-PYRAZOLINES ANTIDEPRESSANT CYCLOADDITION ALDEHYDE KETONES ALKYNES |
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Description |
Novel carbonylated pyrazole phosphonates have been synthesized as single regioisomers by treating conjugated enones, dienones, tropone, and quinone with the Bestmann-Ohira reagent under KOH/EtOH conditions at room temperature. Through an "interrupted" version of the above reaction, carbonylated spiropyrazoline phosphonates have been synthesized from arylide-necycloalkanones under similar conditions (K(2)CO(3)/EtOH) with absolute regio-and diastereoselectivity. The key structures were confirmed by detailed spectroscopic analysis and X-ray crystallography.
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Publisher |
AMER CHEMICAL SOC
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Date |
2012-06-26T08:58:45Z
2012-06-26T08:58:45Z 2011 |
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Type |
Article
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Identifier |
JOURNAL OF ORGANIC CHEMISTRY,76(11)4764-4770
0022-3263 http://dx.doi.org/10.1021/jo200582z http://dspace.library.iitb.ac.in/jspui/handle/100/14242 |
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Language |
English
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