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Synthesis 2022; 54(08): 2019-2030
DOI: 10.1055/a-1681-7480
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
We are grateful for the support provided for this study by the National Natural Science Foundation of China (21871035, 21502013) and the Chongqing Research Program of Basic Research and Frontier Technology (cstc2019jcyj-msxm2653).
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 - indolizinoindolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1681-7480.
- Supporting Information
Publication History
Received: 27 September 2021
Accepted after revision: 28 October 2021
Accepted Manuscript online:
28 October 2021
Article published online:
06 December 2021
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For selected examples, see:
For reviews, see:
For reviews on dearomatization, see:
For selected examples of the synthesis of multisubstituted pyrroles using enamino carbonyl compounds, see:
For examples of the synthesis of heterocycle-tethered multisubstituted pyrroles, see:
For reviews on transformations of enamino ketones, see: