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路易斯酸促进的构建官能化咔唑及其杂环基序的近期合成策略。

Recent synthetic strategies for the construction of functionalized carbazoles and their heterocyclic motifs enabled by Lewis acids.

作者信息

Kumar Marappan Pradeep, G Mahantesh, Amaladass P, Manikandan Chitrarasu, Dhayalan Vasudevan

机构信息

Department of Chemistry, National Institute of Technology Puducherry Karaikal-609609 Union Territory Puducherry India https://vasudeva49.wixsite.com/catalysislab

Department of Chemistry, Madanapalle Institute of Technology & Science Madanapalle 517325 Andhra Pradesh India.

出版信息

RSC Adv. 2023 Nov 6;13(46):32596-32626. doi: 10.1039/d3ra06396h. eCollection 2023 Oct 31.

Abstract

This article demonstrates recent innovative cascade annulation methods for preparing functionalized carbazoles and their related polyaromatic heterocyclic compounds enabled by Lewis acid catalysts. Highly substituted carbazole scaffolds were synthesized Lewis acid mediated Friedel-Crafts arylation, electrocyclization, intramolecular cyclization, cycloaddition, C-N bond-formations, aromatization and cascade domino reactions, metal-catalyzed, iodine catalyzed reactions and multi-component reactions. This review article mainly focuses on Lewis acid-mediated recent synthetic methods to access a variety of electron-rich and electron-poor functional groups substituted carbazole frameworks in one-pot reactions. Polyaromatic carbazole and their related nitrogen-based heterocyclic compounds were found in several synthetic applications in pharma industries, energy devices, and materials sciences. Moreover, the review paper briefly summarised new synthetic strategies of carbazole preparation approaches will assist academic and pharma industries in identifying innovative protocols for producing poly-functionalized carbazoles and related highly complex heterocyclic compounds and discovering active pharmaceutical drugs or carbazole-based alkaloids and natural products.

摘要

本文展示了近期通过路易斯酸催化剂实现的用于制备功能化咔唑及其相关多环芳族杂环化合物的创新级联环化方法。通过路易斯酸介导的傅克芳基化反应、电环化反应、分子内环化反应、环加成反应、C-N键形成反应、芳构化反应和级联多米诺反应、金属催化反应、碘催化反应以及多组分反应,合成了高度取代的咔唑骨架。这篇综述文章主要关注路易斯酸介导的近期合成方法,这些方法能够通过一锅法反应获得各种富电子和缺电子官能团取代的咔唑骨架。多环芳族咔唑及其相关的含氮杂环化合物在制药行业、能源设备和材料科学的多个合成应用中被发现。此外,该综述文章简要总结了咔唑制备方法的新合成策略,这将有助于学术界和制药行业确定用于生产多官能团化咔唑及相关高度复杂杂环化合物的创新方案,并发现活性药物或咔唑类生物碱及天然产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e46/10626344/81cf4111ecb5/d3ra06396h-f1.jpg

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