Efficient and Regioselective One-Pot Synthesis of 3-Substituted and 3,5-Disubstituted Isoxazoles

A series of 3-substituted and 3,5-disubstituted isoxazoles have been efficiently synthesized in moderate to excellent yields by the reaction of N-hydroxyl-4-toluenesulfonamide with α,β-unsaturated aldehydes/ketones. This novel strategy is associated with readily available starting materials, mild co...

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Published inOrganic letters Vol. 11; no. 17; pp. 3982 - 3985
Main Authors Tang, Shibing, He, Jinmei, Sun, Yongquan, He, Liuer, She, Xuegong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.09.2009
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Sulfonamides - chemistry
Toluene - analogs & derivatives
Toluene - chemistry
CONVENIENT SYNTHESIS
NUCLEOPHILES
ELECTROPHILIC CYCLIZATION
CYCLOADDITION
COPPER(I)-CATALYZED SYNTHESIS
HYDROXAMIC ACIDS
5-SUBSTITUTED ISOXAZOLES
RING-OPENING REACTIONS
BENZONITRILE OXIDES
DERIVATIVES
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Summary:A series of 3-substituted and 3,5-disubstituted isoxazoles have been efficiently synthesized in moderate to excellent yields by the reaction of N-hydroxyl-4-toluenesulfonamide with α,β-unsaturated aldehydes/ketones. This novel strategy is associated with readily available starting materials, mild conditions, high regioselectivity, and wide scope.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol901626n