Synthesis of 4-Arylsulfonylquinolines by Double Condensation of Allyl Aryl Sulfones with Nitroarenes

Allyl aryl sulfones 2 react with aryl nitrocompounds 1 in a DBU/MgCl2 system giving the 4‐arylsulfonyl quinolines 3. Some mechanistic aspects of the reaction are discussed. Application of this reaction to the formal total synthesis of the natural product (−)Eupolauramine is described.

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2000; no. 3; pp. 521 - 525
Main Author Wrobel, Z
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 01.02.2000
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Allyl aryl sulfones
Chemistry
Chemistry, Organic
Condensation reaction
Lewis acids
Nitroarenes
Physical Sciences
Science & Technology
condensation reaction
EUPOLAURAMINE
nitroarenes
DIMETHYL PHOSPHITE
Lewis acids
allyl aryl sulfones
ORGANIC-ANIONS
MEDIATED DIRECT CONDENSATION
DERIVATIVES
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Summary:Allyl aryl sulfones 2 react with aryl nitrocompounds 1 in a DBU/MgCl2 system giving the 4‐arylsulfonyl quinolines 3. Some mechanistic aspects of the reaction are discussed. Application of this reaction to the formal total synthesis of the natural product (−)Eupolauramine is described.
Bibliography:istex:997320C563904423443C6FD653250D9DC116F697
ark:/67375/WNG-6Z6FRRK8-V
ArticleID:EJOC521
ISSN:1434-193X
1099-0690
DOI:10.1002/(SICI)1099-0690(200002)2000:3<521::AID-EJOC521>3.0.CO;2-A