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Synthesis 2011(16): 2629-2638  
DOI: 10.1055/s-0030-1260118
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Furan Ring Opening - Pyridine Ring Closure: New Route to Quinolines under the Bischler-Napieralski Reaction Conditions

Alexander V. Butin*a, Fatima A. Tsiunchika, Olga N. Kostyukovaa, Maxim G. Uchuskina, Igor V. Trushkovb,c
a Research Institute of Heterocyclic Compounds Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
Fax: +7(861)2596592; e-Mail: alexander_butin@mail.ru; e-Mail: av_butin@yahoo.com;
b Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation
c Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology and Immunology, Leninskii av. 117/2, Moscow 117997, Russian Federation
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Publication History

Received 18 April 2011
Publication Date:
14 July 2011 (online)

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Abstract

A new approach to highly functionalized quinolines is proposed. This approach is based on the electrophilic recyclization of 2-[2-(acylamino)benzyl]furans under the Bischler-Napieralski reaction conditions.

Key words

furans - ring opening - ring closure - fused-ring systems - quinolines - Bischler-Napieralski reaction

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22

CCDC 820334 (for 3a) contains the supplementary crystallographic data for this paper. Copies of the data can be obtained, free of charge, on application to the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif.