Multicomponent Reactions Involving Arynes, Quinolines, and Aldehydes

The multicomponent reaction involving arynes, quinolines, and aldehydes leading to the diastereoselective synthesis of benzoxazino quinoline derivatives in good yields proceeding via 1,4-zwitterionic intermediates is reported. In addition, the synthetic potential of various carbonyl compounds in thi...

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Published inOrganic letters Vol. 15; no. 17; pp. 4620 - 4623
Main Authors Bhunia, Anup, Porwal, Digvijay, Gonnade, Rajesh G, Biju, Akkattu T
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.09.2013
Amer Chemical Soc
Subjects
aldehydes
carbonyl compounds
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
diastereoselective synthesis
Lewis bases
Physical Sciences
quinoline
Science & Technology
DMAD ZWITTERION
3-COMPONENT REACTION
DIELS-ALDER REACTION
N-HETEROAROMATICS
COUPLING REACTION
REGIOSELECTIVE SYNTHESIS
1,4-DIPOLAR CYCLOADDITION
TERMINAL ALKYNES
CARBON-CARBON
STRAIGHTFORWARD ACCESS
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Summary:The multicomponent reaction involving arynes, quinolines, and aldehydes leading to the diastereoselective synthesis of benzoxazino quinoline derivatives in good yields proceeding via 1,4-zwitterionic intermediates is reported. In addition, the synthetic potential of various carbonyl compounds in this reaction as well as the utility of isoquinoline as the nucleophilic trigger has been examined.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol4023134