Iron-Catalyzed One-Pot Synthesis of Indole-Tethered Tetrasubstituted Pyrroles and Their Transformations to Indolizino[8,7-b]indole Derivatives

Xue Xiao; Xiao-Hui Chen; Xian-Xun Wang; Wan-Zhen Li; Hai-Lei Cui

doi:10.1055/a-1681-7480

Synthesis, Table of Contents

Synthesis 2022; 54(08): 2019-2030
DOI: 10.1055/a-1681-7480

paper

Iron-Catalyzed One-Pot Synthesis of Indole-Tethered Tetrasubstituted Pyrroles and Their Transformations to Indolizino[8,7-b]indole Derivatives

Xue Xiao

^aLaboratory of Asymmetric Synthesis, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing, 402160, P. R. of China

^bTonichem Pharmaceutical Technology Co., Ltd, Huizhou, 516008, P. R. of China

,

Xiao-Hui Chen

^aLaboratory of Asymmetric Synthesis, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing, 402160, P. R. of China

^bTonichem Pharmaceutical Technology Co., Ltd, Huizhou, 516008, P. R. of China

,

Xian-Xun Wang

^bTonichem Pharmaceutical Technology Co., Ltd, Huizhou, 516008, P. R. of China

,

Wan-Zhen Li

^aLaboratory of Asymmetric Synthesis, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing, 402160, P. R. of China

,

Hai-Lei Cui ∗

^aLaboratory of Asymmetric Synthesis, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing, 402160, P. R. of China

› Author Affiliations

Abstract

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Abstract

We have developed an efficient iron-catalyzed one-pot reaction of tryptamines, ynones and nitroolefins, affording indole-tethered tetrasubstituted pyrroles in acceptable to good yields. Other aromatic and aliphatic amines can also be utilized in this process, delivering the corresponding highly functionalized tetrasubstituted pyrroles. Indolizino[8,7-b]indole derivatives could be obtained through TFA-, TfOH- or Fe(OTf)₃-mediated cyclizations via dearomatization of indole. Unexpected dibrominated products, 7,9-dibromo-6,11-dihydro-5H-indolizino[8,7-b]indoles, were formed when trimethylphenylammonium tribromide (PTAP) was employed as electrophilic cyclization promoter.

Key words

one pot - iron salts - trifluoromethanesulfonic acid - ynones - pyrroles - indolizinoindoles

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References

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