新型苯并咪唑基取代丙烯腈和脒基取代苯并咪唑并[1,2-a]喹啉的合成
Synthesis of novel benzimidazolyl-substituted acrylonitriles and amidino-substituted benzimidazo[1,2-a]quinolines.
作者信息
Hranjec Marijana, Karminski-Zamola Grace
机构信息
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, Marulićev trg 20, HR-10000 Zagreb, Croatia.
出版信息
Molecules. 2006 Aug 13;12(8):1817-28. doi: 10.3390/12081817.
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.
摘要
合成了一系列新型苯并咪唑衍生物3-10。苯并咪唑基取代的丙烯腈3和4发生光化学脱氢环化反应，生成相应的单氰基和二氰基取代的苯并咪唑并[1,2-a]喹啉5和6。这些化合物的平纳反应并未得到预期的单脒和二脒，而是仅分离出了在6位带有酰胺基的化合物7-10。提出了该反应的机理。无环化合物3和4以及环状苯并咪唑并[1,2-a]喹啉5-8表现出有趣的光谱性质，是潜在的生物活性化合物。
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