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Synthesis 2009(14): 2393-2402  
DOI: 10.1055/s-0029-1217396
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of Fluorinated Benzofuro- and Benzothieno[2,3-b]pyridines, α-Carbolines and Nucleosides Containing the α-Carboline Framework

Viktor O. Iaroshenko*a,b, Yan Wangc, Biao Zhangc, Dmitriy Volochnyukd, Vyacheslav Ya. Sosnovskikhe
a Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kiev 33, Ukraine
c Fachbereich Chemie, Universität Konstanz, Fach M-720, Universitätsstr. 10, 78457 Konstanz, Germany
d Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kiev 94, Ukraine
e Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
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Publikationsverlauf

Received 24 December 2008
Publikationsdatum:
22. Juni 2009 (online)

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Abstract

Fluorinated benzofuro[2,3-b]pyridines, benzo­thieno[2,3-b]pyridines and 9H-pyrido[2,3-b]indoles (α-carbolines) were synthesized via regiospecific pyridine core annulation of a number of fluoro-containing 1,3-CCC-dielectrophiles to benzofuran-2-amine, benzothiophen-2-amine and 1H-indol-2-amine. Based on the 2,4-bis(trifluoromethyl)-9H-pyrido[2,3-b]indole thus synthesized, the preparative approach towards a set of nucleosides and nucleoside mimetics bearing the α-carboline framework was elaborated.

Key words

pyridines - fluorine - annulation - functionalization - α-carbolines - nucleosides

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