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

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

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 5 , 2015

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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.

Keywords: Benzimidazole, bioactive units, combination, Csp2-N bond formation, 2(5H)-furanone, metal-free catalysis, Michael addition-elimination reaction, one-pot synthesis.

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Article Details

VOLUME: 12
ISSUE: 5
Year: 2015
Page: [359 - 370]
Pages: 12
DOI: 10.2174/1570178612666150305002655
Price: $65

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