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
Online AccessGet full text
ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/ol300872e

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Abstract 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.
AbstractList 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.
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.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.
Author Wang, Liangguang
Bao, Ming
Feng, Xiujuan
Yu, Xiaoqiang
AuthorAffiliation Dalian University of Technology
AuthorAffiliation_xml – name: Dalian University of Technology
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  surname: Wang
  fullname: Wang, Liangguang
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  email: yuxiaoqiang@dlut.edu.cn, mingbao@dlut.edu.cn
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  givenname: Xiujuan
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  fullname: Feng, Xiujuan
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  surname: Bao
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  email: yuxiaoqiang@dlut.edu.cn, mingbao@dlut.edu.cn
BackLink https://www.ncbi.nlm.nih.gov/pubmed/22537143$$D View this record in MEDLINE/PubMed
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Issue 9
Keywords ELECTROPHILIC CYCLIZATION
CYCLOADDITION
COPPER(I)-CATALYZED SYNTHESIS
ONE-POT SYNTHESIS
ALKYNYL OXIME ETHERS
REGIOSELECTIVE SYNTHESIS
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Snippet An efficient method for the synthesis of 3,5-disubstituted isoxazoles is described. The reactions of 1,3-dialkynes with hydroxylamine proceeded smoothly in...
An efficient method for the synthesis of 3,5-disubstituted Isoxazoles is described. The reactions of 1,3-dialkynes with hydroxylamine proceeded smoothly in...
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SubjectTerms 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
Title Synthesis of 3,5-Disubstituted Isoxazoles via Cope-Type Hydroamination of 1,3-Dialkynes
URI http://dx.doi.org/10.1021/ol300872e
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https://www.ncbi.nlm.nih.gov/pubmed/22537143
https://www.proquest.com/docview/1011198371
https://www.proquest.com/docview/2010204382
Volume 14
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