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Isoxazoles from 1,1-Disubstituted Bromoalkenes.

ABSTRACT: The regioselective synthesis of 3,5-disubstituted isoxazoles was achieved through the 1,3-dipolar cycloaddition of nitrile oxides with 1,1-disubstituted bromoalkenes. The substituted bromoalkenes function as alkyne synthons which were used to construct 5,5-disubstituted bromoisoxazoline intermediates that aromatize to the analogous isoxazoles through the loss of HBr.

SUBMITTER: Dadiboyena S

PROVIDER: S-EPMC2031838 | biostudies-literature | 2007 Feb

REPOSITORIES: biostudies-literature

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Isoxazoles from 1,1-Disubstituted Bromoalkenes.

Dadiboyena Sureshbabu S Xu Jianping J Hamme Ashton T AT

Tetrahedron letters 20070201 7

The regioselective synthesis of 3,5-disubstituted isoxazoles was achieved through the 1,3-dipolar cycloaddition of nitrile oxides with 1,1-disubstituted bromoalkenes. The substituted bromoalkenes function as alkyne synthons which were used to construct 5,5-disubstituted bromoisoxazoline intermediates that aromatize to the analogous isoxazoles through the loss of HBr. ...[more]

PMID: 18265873

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