原创力文档synthesis of novel benzimidazolyl-substituted acrylonitriles and amidino-substituted benzimidazo[1,2-a]quinolines合成新型benzimidazolyl-substituted丙烯腈和amidino-substituted benzimidazo(1 a)喹啉类药物.pdfVIP
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synthesis of novel benzimidazolyl-substituted acrylonitriles and amidino-substituted benzimidazo[1,2-a]quinolines合成新型benzimidazolyl-substituted丙烯腈和amidino-substituted benzimidazo(1 a)喹啉类药物
Molecules 2007, 12, 1817-1828
molecules
ISSN 1420-3049
© 2007 by MDPI
/molecules
Full Paper
Synthesis of Novel Benzimidazolyl-substituted Acrylonitriles
and Amidino-substituted Benzimidazo[1,2-a]Quinolines
Marijana Hranjec and Grace Karminski-Zamola*
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, Marulićev trg
20, HR-10000 Zagreb, Croatia
* Author to whom correspondence should be addressed; E-mail: gzamola@fkit.hr;
Phone: +385 1 4597 215; Fax: +385 1 4597 224
Received: 28 June 2007; in revised form: 20 July 2007 / Accepted: 20 July 2007 / Published: 13
August 2007
Abstract: A series of novel benzimidazole derivatives 3-10 were synthesized.
Benzimidazolyl-substituted acrylonitriles 3 and 4 underwent a photochemical dehydro-
cyclization reaction to give the corresponding mono- and dicyano-substituted
benzimidazo[1,2-a] quinolines 5 and 6. Pinner reaction of these compounds did not give
the expected mono- and diamidines, but rather only compounds 7-10, with amido groups at
6-position were isolated. A mechanism for the reaction is proposed. Acyclic compounds 3
and 4, as well as cyclic benzimidazo[1,2-a]quinolines 5-8, exhibit interesting spectroscopic
properties and are potential biologically active compounds.
Keywords: Benzimidazoles, acrylonitriles, amidines, benzimidazo[1,2-a]quinolines,
Pinner reaction.
Introduction
Over the past years substituted benzimidazoles and their azino fused derivatives have been one of
the m
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