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Synthesis 2007(18): 2872-2886  
DOI: 10.1055/s-2007-983842
PAPER
© Georg Thieme Verlag Stuttgart · New York

A One-Pot Fusion of Nitrogen-Containing Heterocycles

Sergey V. Ryabukhina,b, Andrey S. Plaskona,b, Dmitriy M. Volochnyuk*a,c, Alexander N. Shivanyukb, Andrey A. Tolmachevb
a ‘Enamine Ltd.’, 23 A. Matrosova Street, 01103 Kyiv, Ukraine
b National Taras Shevchenko University, 62 Volodymyrska Street, 01033 Kyiv, Ukraine
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
Further Information

Publication History

Received 25 April 2007
Publication Date:
08 August 2007 (online)

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Abstract

Aromatic and heteroaromatic dialkylaminoaldehydes react with various active methylene compounds in the presence of Me3SiCl to give functionally and structurally diverse pyrrolo[1,2-a]quinolines, pyrido[1,2-a]quinolines, pyrazolo[3,4-e]indolizines, pyrazolo[4,3-c]quinolizines, benzo[g]pyrrolo[1,2-a]-1,8-naphthyridines, and benzo[g]pyrido[1,2-a]-1,8-naphthyridines in high yield and excellent purity.

Key words

pyrazolo[3,4-e]indolizines - pyrazolo[4,3-c]quinolizines - benzo[g]pyrido[1,2-a]-1,8-naphthyridines - ortho-dialkylaminoaldehydes - chlorotrimethylsilane - tert-amino effect