Synthesis of 3,5-Disubstituted Isoxazoles via Cope-Type Hydroamination of 1,3-Dialkynes

An efficient method for the synthesis of 3,5-disubstituted isoxazoles is described. The reactions of 1,3-dialkynes with hydroxylamine proceeded smoothly in DMSO under mild reaction conditions to produce 3,5-disubstituted isoxazoles in satisfactory to excellent yields.

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 9; pp. 2418 - 2421
Main Authors Wang, Liangguang, Yu, Xiaoqiang, Feng, Xiujuan, Bao, Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.05.2012
Amer Chemical Soc
Subjects
Amination
Catalysis
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Cyclization
dimethyl sulfoxide
Diynes - chemistry
hydroxylamine
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
ELECTROPHILIC CYCLIZATION
CYCLOADDITION
COPPER(I)-CATALYZED SYNTHESIS
ONE-POT SYNTHESIS
ALKYNYL OXIME ETHERS
REGIOSELECTIVE SYNTHESIS
CONVENIENT
N-OXIDES
EFFICIENT
DERIVATIVES
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/ol300872e

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Summary:An efficient method for the synthesis of 3,5-disubstituted isoxazoles is described. The reactions of 1,3-dialkynes with hydroxylamine proceeded smoothly in DMSO under mild reaction conditions to produce 3,5-disubstituted isoxazoles in satisfactory to excellent yields.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol300872e