A convenient synthesis of beta-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-beta-carbolines under air

Arshad, Ahmad Saifuddin Mohamad and Meesala, Ramu and Hanapi, Nur Aziah and Mordi, Mohd Nizam (2021) A convenient synthesis of beta-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-beta-carbolines under air. Tetrahedron, 83. ISSN 0040-4020, DOI https://doi.org/10.1016/j.tet.2021.131960.

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Abstract

A convenient synthesis for the conversion of various substituted tetrahydro-beta-carbolines has been developed by iron-catalyzed decarboxylative/dehydrogenative aromatization to construct aromatic beta-carbolines under air atmosphere. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce corresponding beta-carbolines in good yields in the absence of any additive. Additionally, the utility of the method was highlighted in the gram-scale synthesis of important natural beta-carboline synthons norharmane (2a) and harmane (2b), which the latter provide practical access towards eudistomin N and nostocarboline. (C) 2021 Elsevier Ltd. All rights reserved.

Item Type: Article
Funders: Universiti Sains Malaysia [1001/CDADAH/8011075], Institute of Postgraduate Studies, USM
Uncontrolled Keywords: Beta-carbolines; Decarboxylative aromatization; Dehydrogenative aromatization; Iron; Tetrahydro-beta-carbolines
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 15 Apr 2022 04:43
Last Modified: 15 Apr 2022 04:43
URI: http://eprints.um.edu.my/id/eprint/26782

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