Chinese Journal of Organic Chemistry >
One-Pot Synthesis of 1,5-Benzodiazepine Compounds by Three-Component Tadem Reaction
Received date: 2020-06-20
Revised date: 2020-09-03
Online published: 2020-10-15
Supported by
the National Natural Science Foundation of China(21776060); the Natural Science Foundation of Hebei Province(B2016205165)
43 novel 1,5-benzodiazepine compounds were obtained via one-pot multicomponent and tadem reactions for 2~5 h and the yield of the target compounds is up to 95%. These reactions were achieved by reacting substituted 1,2-phenylene- diamines, 1,3-cyclopentanedione or 1,3-cyclohexanedione (5,5-dimethyl-1,3-cyclohexanedione), 2,3-dicarbonyl compounds with p-toluenesulfonic acid as catalyst in EtOH. The active intermediates with the imine and enamine structures in the molecule were formed by two nucleophilic addition-dehydration processes and then 1,5-benzodiazepine compounds were obtained via carbon-carbon coupling cyclization and proton transfer processes, which realized the construction of one new seven- membered ring and four new chemical bonds (two C—N, one C=C, one C—C) in one-pot. It provides a green, environmentally friendly, efficient and simple synthetic thought for the synthesis of 1,5-benzodiazepine compounds.
Key words： 1,5-benzodiazepine compound; tadem reaction; green synthesis; mechanism
Jing Li , Zhenfang Hao , Kaiyue Zhang , Lanzhi Wang . One-Pot Synthesis of 1,5-Benzodiazepine Compounds by Three-Component Tadem Reaction[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 806 -818 . DOI: 10.6023/cjoc202006040
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