Synthesis of Elaborate Benzofuran-2-carboxamide Derivatives Through a Combination of 8-Aminoquinoline Directed C-H Arylation and Transamidation Chemistry

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2020 Jan 19

PMID 31952313

Citations 2

Authors

Michael Oschmann

Linus Johansson Holm

Monireh Pourghasemi-Lati

Oscar Verho

Affiliations

Soon will be listed here.

Abstract

Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C-H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C-H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate -acyl-Boc-carbamates. Given the high efficiency and modularity of this synthetic strategy, it constitutes a very attractive method for generating structurally diverse collections of benzofuran derivatives for small molecule screening campaigns.

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