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

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

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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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