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Molecules 2007, 12(8), 1817-1828; doi:10.3390/12081817

Synthesis of Novel Benzimidazolyl-substituted Acrylonitriles and Amidino-substituted Benzimidazo[1,2-a]Quinolines

Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, Marulićev trg 20, HR-10000 Zagreb, Croatia
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Received: 28 June 2007 / Revised: 20 July 2007 / Accepted: 20 July 2007 / Published: 13 August 2007
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Abstract

A series of novel benzimidazole derivatives 3-10 were synthesized. Benzimidazolyl-substituted acrylonitriles 3 and 4 underwent a photochemical dehydrocyclization 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. Benzimidazoles; acrylonitriles; amidines; benzimidazo[1; 2-a]quinolines; Pinner reaction.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Hranjec, M.; Karminski-Zamola, G. Synthesis of Novel Benzimidazolyl-substituted Acrylonitriles and Amidino-substituted Benzimidazo[1,2-a]Quinolines. Molecules 2007, 12, 1817-1828.

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