Tandem Synthesis of 2,3-Dihydro-4-iminoquinolines via Three-Component Alkyne-Imine Metathesis

In the absence of any catalysts, ortho-alkynylanilines react with aldehydes and amines in HFIP to form trans-2,3-disubstituted 2,3-dihydro-4-iminoquinolines in a complete trans-selective manner via the three-component alkyne-imine metathesis.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 75; no. 20; pp. 6980 - 6982
Main Authors Saito, Akio, Kasai, Jun, Konishi, Tomoyo, Hanzawa, Yuji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.10.2010
Amer Chemical Soc
Subjects
Alkynes - chemistry
Chemistry
Chemistry, Organic
Imines - chemistry
Molecular Structure
Physical Sciences
Quinolines - chemical synthesis
Quinolines - chemistry
Science & Technology
Stereoisomerism
ANTITUMOR POLYCYCLIC ACRIDINES
ACIDS
COUPLING REACTION
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Summary:In the absence of any catalysts, ortho-alkynylanilines react with aldehydes and amines in HFIP to form trans-2,3-disubstituted 2,3-dihydro-4-iminoquinolines in a complete trans-selective manner via the three-component alkyne-imine metathesis.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo1013993