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

doi:10.3390/12081817

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

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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.

Received: 28 June 2007; in revised form: 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.

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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.

AMA Style

Hranjec M, Karminski-Zamola G. Synthesis of Novel Benzimidazolyl-substituted Acrylonitriles and Amidino-substituted Benzimidazo[1,2-a]Quinolines. Molecules. 2007; 12(8):1817-1828.

Chicago/Turabian Style

Hranjec, Marijana; Karminski-Zamola, Grace. 2007. "Synthesis of Novel Benzimidazolyl-substituted Acrylonitriles and Amidino-substituted Benzimidazo[1,2-a]Quinolines." Molecules 12, no. 8: 1817-1828.

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