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

Document Type

Article

Publication Date

3-12-2021

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.

Keywords

Beta-carbolines, Decarboxylative aromatization, Dehydrogenative aromatization, Iron, Tetrahydro-beta-carbolines

Publication Title

Tetrahedron

Divisions

CHEMISTRY

Funders

Universiti Sains Malaysia [1001/CDADAH/8011075],Institute of Postgraduate Studies, USM

Volume

83

Publisher

Elsevier

Publisher Location

THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND

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