1,3-Dipolar cycloaddition route to novel isoxazole-type derivatives related to combretastatin A-4

Graphic A series of compounds related to combretastatin A-4, containing a five-membered heterocyclic ring interposed between the two phenyl groups have been prepared. Synthetic approach involves 1,3-dipolar cycloaddition of various 3,4,5-trimethoxyphenyl units with an in situ generated nitrile oxide...

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Bibliographic Details
Published in:Tetrahedron letters 2004-04, Vol.45 (17), p.3359-3362
Main Authors: Kaffy, Julia, Monneret, Claude, Mailliet, Patrick, Commerçon, Alain, Pontikis, Renée
Format: Article
Language:English
Subjects:
1,3-Dipolar cycloaddition
Combretastatin
Nitrile oxide
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Summary:Graphic A series of compounds related to combretastatin A-4, containing a five-membered heterocyclic ring interposed between the two phenyl groups have been prepared. Synthetic approach involves 1,3-dipolar cycloaddition of various 3,4,5-trimethoxyphenyl units with an in situ generated nitrile oxide from a suitable aldoxime using sodium hypochlorite. Depending on the nature of the dipolarophile, 3,5-diarylisoxazole derivatives were obtained along with the 3,4-regioisomeric isomers.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.03.020