Issue 9, 2009

Synthesis of chromones and 4-hydroxyquinolines based on uncatalyzed condensations of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-alkoxy- and 2-nitrobenzoyl chlorides and related reactions

Abstract

The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-methoxybenzoyl chlorides afforded 3,5-diketoesters which were transformed, by treatment with boron tribromide, into functionalized 2-hydroxychroman-4-ones or chromones. The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-nitrobenzoyl chlorides and subsequent reduction of the nitro group afforded functionalized 4-hydroxyquinolines. Their tautomeric equilibrium was studied by NMR spectroscopy and by computational methods.

Graphical abstract: Synthesis of chromones and 4-hydroxyquinolines based on uncatalyzed condensations of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-alkoxy- and 2-nitrobenzoyl chlorides and related reactions

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2009
Accepted
20 Feb 2009
First published
20 Mar 2009

Org. Biomol. Chem., 2009,7, 1931-1938

Synthesis of chromones and 4-hydroxyquinolines based on uncatalyzed condensations of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-alkoxy- and 2-nitrobenzoyl chlorides and related reactions

T. Rahn, B. Appel, W. Baumann, H. Jiao, A. Börner, C. Fischer and P. Langer, Org. Biomol. Chem., 2009, 7, 1931 DOI: 10.1039/B901092K

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