A Facile Route to Imidazo[1,2-a]quinolines via a Domino Reaction

Rustam T. Iminov; Anton V. Tverdokhlebov; Andrey A. Tolmachev; Yulian M. Volovenko; Alexander N. Kostyuk; Alexander N. Chernega; Eduard B. Rusanov

doi:10.1055/s-2008-1072572

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Synthesis 2008(10): 1535-1540
DOI: 10.1055/s-2008-1072572

PAPER

A Facile Route to Imidazo[1,2-a]quinolines via a Domino Reaction

Rustam T. Iminov^a, Anton V. Tverdokhlebov*^b, Andrey A. Tolmachev^b, Yulian M. Volovenko^a, Alexander N. Kostyuk^c, Alexander N. Chernega^c, Eduard B. Rusanov^c
^a Kiev National Taras Shevchenko University, Volodimirska str. 62, 01033 Kiev, Ukraine
^b Enamine Ltd., Alexandra Matrosova str. 23, 01103 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: atver@univ.kiev.ua;
^c Institute of Organic Chemistry, National Academy of Sciences, Murmanska str. 5, 02094 Kiev, Ukraine

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Publication History

Received 9 January 2008
Publication Date:
27 March 2008 (online)

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Abstract

The interaction of methyl 2,4-dioxo-2H-3,1-benzoxazine-1(4H)-acetate, 1-(3,3-dimethyl-2-oxobutyl)- and 1-(2-oxopropyl)-2H-3,1-benzoxazine-2,4(1H)-diones with substituted acetonitriles, XCH₂CN (X = CN, hetaryl), has been studied. In acetic acid in the presence of sodium acetate, imidazo[1,2-a]quinoline-2,5(1H,3H)-diones, 2-tert-butyl- and 2-methylimidazo[1,2-a]quinolin-5(3H)-ones were obtained in 60-85% yield. A reaction pathway is suggested and has been confirmed by the isolation of specific intermediates. The scope and limitations of the method are discussed. The structure of the obtained imidazo[1,2-a]quinoline derivatives has been assigned unambiguously on the basis of an X-ray crystallographic study.

Key words

cyclizations - domino reactions - heterocycles - imidazo[1,2-a]quinolines - nitriles

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