Molecular-iodine catalyzed selective construction of cyclopenta[b]indoles from indoles and acetone: a green gateway to indole-fused cycles

文献信息

发布日期 2023-10-31
DOI 10.1039/D3OB01561K
影响因子 3.876
作者

Bipul Sarma, Utpal Bora


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摘要

Molecular-iodine catalyzed access to an important class of bio-relevant indole derivatives, cyclopenta[b]indoles, has been achieved via a cascade addition/intramolecular cyclization reaction of indoles and acetone. Explorations of diverse substitution patterns revealed an essential substrate-control in the reaction. The high-density electronic core of indole is pivotal in favouring the formation of indolyl-cyclopenta[b]indole derivatives; in contrast, the electron deficiency of the core hindered the cyclization process, directing the formation of bis(indolyl)propanes. Investigations on the mechanistic pathway revealed that bis(indolyl)alkanes were the intermediates for the addition–cyclization process. This simple experimental method provides sustainable synthetic access to cyclopentannulated indoles.

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Contents

Front/Back Matter

DOI: 10.1039/B508441P

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来源期刊

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
自引率: 10.3%
年发文量: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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