One-Pot Synthesis of 5-Alkoxy-4-amino-3-halo-2(5H)-furanones Containing Benzimidazole Moiety in the Absence of Metal Catalyst

Title:One-Pot Synthesis of 5-Alkoxy-4-amino-3-halo-2(5H)-furanones Containing Benzimidazole Moiety in the Absence of Metal Catalyst

Volume: 12 Issue: 5

Author(s): Pai Peng, Min-Hua Feng, Jie Shi, Jia-Li Zheng, Yan-Cheng Wu, Zhao-Yang Wang and Ren-Hong Chen

Affiliation:

Keywords: Benzimidazole, bioactive units, combination, C_sp2-N bond formation, 2(5H)-furanone, metal-free catalysis, Michael addition-elimination reaction, one-pot synthesis.

Abstract: In the presence of KF as base and THF as solvent, the tandem Michael addition-elimination reaction of different 5-alkoxy-3,4-dihalo-2(5H)-furanones with aminomethyl benzimidazoles at room temperature gave 21 target compounds simultaneously containing both bioactive benzimidazole and 2(5H)-furanone moieties in yields of 62-88 % (mostly over 71 %). The structures of all the newly synthesized compounds were elucidated and confirmed by FTIR, UV, ¹H NMR, ¹³C NMR, mass spectroscopy and elemental analysis. The simple one-pot synthetic method provides a brief route for the introduction of the benzimidazole unit into 2(5H)-furanone derivatives under mild conditions without any metal catalysts. This transformation also affords an important synthetic strategy for the series 2(5H)-furanone derivatives, as well as a basis for the activity test of these potential drug molecules.

Cite this article as:

Peng Pai, Feng Min-Hua, Shi Jie, Zheng Jia-Li, Wu Yan-Cheng, Wang Zhao-Yang and Chen Ren-Hong, One-Pot Synthesis of 5-Alkoxy-4-amino-3-halo-2(5H)-furanones Containing Benzimidazole Moiety in the Absence of Metal Catalyst, Letters in Organic Chemistry 2015; 12 (5) . https://dx.doi.org/10.2174/1570178612666150305002655