Chinese Journal of Organic Chemistry >
Basicity-Tuned Selectivity: Synthesis of Benzimidazolone and Benzodiazepine from N-Alkyl-N-(2-(pyridin-2-ylamino)-phenyl)formamides
Received date: 2021-07-29
Revised date: 2021-09-29
Online published: 2021-12-31
Supported by
Xinjiang Bingtuan Young and Middle-Aged Leading Scientists Program(2020CB027); Shihezi Young and Middle-Aged Leading Scientists Program(2019RC01); Open Sharing Fund for the Large-scale Instruments and Equipment of Shihezi University.
A base-controlled strategy for the selective preparation of benzimidazolone and pyrido-benzodiazepine derivatives was developed. The N-alkyl-N-(2-(pyridin-2-ylamino)phenyl)formamides underwent selective coupling to synthesize a series of benzimidazolones when NaOAc was used as bases and employed K2S2O8 as oxidants. By changing bases to NaHCO3, a series of benzodiazepines was obtained. The possible reaction mechanism was proposed based on the radical-trapping experiments. The applicability of this protocol is demonstrated by scale-up experiments and the functionalization of benzodiazepine products.
Key words： benzimidazolone; benzodiazepine; oxidant-induced; metal-free
Yubin Wang , Cheng Guo , Sheng Tao , Jichang Liu , Jigang Zhao , Ning Liu , Bin Dai . Basicity-Tuned Selectivity: Synthesis of Benzimidazolone and Benzodiazepine from N-Alkyl-N-(2-(pyridin-2-ylamino)-phenyl)formamides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1146 -1162 . DOI: 10.6023/cjoc202107062
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