A One-Pot Fusion of Nitrogen-Containing Heterocycles

Sergey V. Ryabukhin; Andrey S. Plaskon; Dmitriy M. Volochnyuk; Alexander N. Shivanyuk; Andrey A. Tolmachev

doi:10.1055/s-2007-983842

PAPER

A One-Pot Fusion of Nitrogen-Containing Heterocycles

Sergey V. Ryabukhin^a,b, Andrey S. Plaskon^a,b, Dmitriy M. Volochnyuk*^a,c, Alexander N. Shivanyuk^b, Andrey A. Tolmachev^b
^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;

Abstract

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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

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