中国化学快报(英文版)2024，Vol.35Issue(7) ：247-252.DOI:10.1016/j.cclet.2023.109280

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

Xiao Xiao Biao Chen Jia-Wei Li Jun-Bo Zheng Xu Wang Hang Zhao Fen-Er Chen
中国化学快报(英文版)2024，Vol.35Issue(7) ：247-252.DOI:10.1016/j.cclet.2023.109280
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Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow

Xiao Xiao 1Biao Chen 1Jia-Wei Li 1Jun-Bo Zheng 1Xu Wang 1Hang Zhao 1Fen-Er Chen2
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作者信息

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

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.

Key words

Tryptamines and tryptophols/Nitrite/Economic and sustainable bromocyclization/HPI and TFI structures/Bath and flow

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基金项目

National Natural Science Foundation of China(22208302)

Natural Science Foundation of Zhejiang Province of China(LQ21B020006)

Natural Science Foundation of Zhejiang Province of China(ZJ2022039)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCDCSCD
影响因子：0.771
ISSN：1001-8417
参考文献量92
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