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Synthesis 2008(10): 1535-1540  
DOI: 10.1055/s-2008-1072572
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Rustam T. Iminova, Anton V. Tverdokhlebov*b, Andrey A. Tolmachevb, Yulian M. Volovenkoa, Alexander N. Kostyukc, Alexander N. Chernegac, Eduard B. Rusanovc
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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Publikationsverlauf

Received 9 January 2008
Publikationsdatum:
27. März 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