Superacid-promoted synthesis of quinoline derivatives

Author ORCID Identifier

Douglas Klumpp:https://orcid.org/0000-0001-5271-699X

Publication Title

Tetrahedron Letters

ISSN

00404039

E-ISSN

43909

Document Type

Article

Abstract

A series of vinylogous imines have been prepared from anilines and cinnamaldehydes. These substrates react in superacidic media to provide quinolines and related compounds. A mechanism for the conversion is proposed which involves the cyclization of dicationic superelectrophilic intermediates. Aromatization of the quinoline ring is thought to occur by superacid-promoted elimination of benzene.

Publication Date

3-19-2020

DOI

10.1016/j.tetlet.2020.151630

Keywords

Heterocycle, Quinoline, Superacid, Superelectrophile

Department

Department of Chemistry and Biochemistry

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