標題: Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization
作者: Yao, Po-Hsin Eric
Kumar, Sunil
Liu, Yu-Li
Fang, Chiu-Ping
Liu, Chia-Chen
Sun, Chung-Ming
應用化學系
Department of Applied Chemistry
關鍵字: Knoevenagel condensation;coumarin;diversity-oriented synthesis;one-pot synthesis;pkDAO activity
公開日期: 1-Apr-2017
摘要: Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent. yields. In situ intramolecular cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanome-thylbenzimidazoles with salicylaldehydes promoted by triethylamine to reach the target compounds. An important intermediate, 2-(2-imino-2H-chromen-3-yl)-1H-benzimidazole was characterized by X-ray analysis and further hydrolyzed to 2-(coumarin-3-yl)benzimidazole in acidic condition. Among the synthesized compounds, some were found to be promising inhibitors of porcine kidney D-amino acid oxidase (pkDAO).
URI: http://dx.doi.org/10.1021/acscombsci.7b00004
http://hdl.handle.net/11536/145351
ISSN: 2156-8952
DOI: 10.1021/acscombsci.7b00004
期刊: ACS COMBINATORIAL SCIENCE
Volume: 19
起始頁: 271
結束頁: 275
Appears in Collections:Articles