A general approach to the synthesis of substituted isoxazolo[4,3-c]quinolines via chalcones
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
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| Creator |
Madapa, Sudharshan
Sridhar, Divya Yadav, G P Maulik, P R Batra, Sanjay |
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| Date |
2007-12-07T07:10:36Z
2007-12-07T07:10:36Z 2007 |
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| Identifier |
European Journal of Organic Chemistry (2007), No. 26, 4343-4351
http://hdl.handle.net/123456789/40 |
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| Description |
A general and practical approach to the synthesis of substituted isoxazolo[4,3-c]quinolines from the substituted isoxazolines afforded by 1,3-dipolar cycloaddition between 2-nitrobenzonitrile oxide and chalcones is described. The SnCl2.2H2O-mediated reduction of the nitro group followed by intramolecular cyclization involving the amino and the keto groups in these substrates furnished a mixture of isoxazolo[4,3- c]-quinolines and 3,5-dihydro-isoxazolo[4,3-c]quinoline. In contrast, the reduction of these substrates with Fe-AcOH unexpectedly yielded 3-benzoyl-4-quinolinamine derivatives.
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| Format |
364285 bytes
application/pdf |
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| Language |
en
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| Relation |
CDRI Communication no. 7159
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| Subject |
Isoxazolo[4,3-c]quinoline
3-benzoyl-4-quinolinamine Reduction Heterocyclization |
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| Title |
A general approach to the synthesis of substituted isoxazolo[4,3-c]quinolines via chalcones
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| Type |
Article
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