Abstract
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-cyanomethylbenzimidazoles 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).
Original language | English |
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Pages (from-to) | 271-275 |
Number of pages | 5 |
Journal | ACS Combinatorial Science |
Volume | 19 |
Issue number | 4 |
DOIs | |
State | Published - 10 Apr 2017 |
Keywords
- Knoevenagel condensation
- coumarin
- diversity-oriented synthesis
- one-pot synthesis
- pkDAO activity