Citation: Xiao Xiao, Biao Chen, Jia-Wei Li, Jun-Bo Zheng, Xu Wang, Hang Zhao, Fen-Er Chen. Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow[J]. Chinese Chemical Letters, ;2024, 35(7): 109280. doi: 10.1016/j.cclet.2023.109280 shu

Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow

Xiao Xiao ^a ,
Biao Chen ^a ,
Jia-Wei Li ^a ,
Jun-Bo Zheng ^a ,
Xu Wang ^a ,
Hang Zhao ^a ,
Fen-Er Chen ^{a, b, c, d, *,}

a.
Institute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China
b.
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
c.
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China
d.
Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China

rfchen@fudan.edu.cn

Received Date: 18 September 2023
Revised Date: 26 October 2023
Accepted Date: 6 November 2023
Available Online: 9 November 2023

Figures(8)

A highly efficient and concise bromocyclization has been successfully achieved, in which tryptamine/tryptophol derivates can be transformed to valuable HPI/TFI scaffolds with economic and green manners. Moreover, a controllable cascade transformation of bromocyclization and aromatic bromination has also been smoothly achieved to form dibrominated HPIs and TFIs. Production could be successfully scaled up under both the batch process and a continuous flow fashion. The most remarkable peculiarity of our process over all previous methods is that the generated water is the major waste. Notably, successful application of this new protocol has been demonstrated by the pharmaceutical and natural products syntheses.
- Tryptamines and tryptophols,
- Nitrite,
- Economic and sustainable bromocyclization,
- HPI and TFI structures,
- Bath and flow
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