Issue 18, 2019

Direct access to benzofuro[2,3-b]quinoline and 6H-chromeno[3,4-b]quinoline cores through gold-catalyzed annulation of anthranils with arenoxyethynes and aryl propargyl ethers

Abstract

This work reports a facile annulation of anthranils with aryloxyethynes or aryl propargyl ethers to construct useful benzofuro[2,3-b]quinoline and 6H-chromeno[3,4-b]quinoline frameworks, respectively; these heterocycles are not readily available from literature methods despite their biological significance. This high atom- and step-economy strategy is highlighted by a broad substrate scope. The reaction mechanism is proposed to proceed through sequential cyclizations among the oxyaryl group, gold carbene and benzaldehyde of the α-imino gold carbene intermediates.

Graphical abstract: Direct access to benzofuro[2,3-b]quinoline and 6H-chromeno[3,4-b]quinoline cores through gold-catalyzed annulation of anthranils with arenoxyethynes and aryl propargyl ethers

Supplementary files

Article information

Article type
Communication
Submitted
25 ⴱⵕⴰ 2019
Accepted
08 ⵉⴱⵔ 2019
First published
09 ⵉⴱⵔ 2019

Org. Biomol. Chem., 2019,17, 4452-4455

Direct access to benzofuro[2,3-b]quinoline and 6H-chromeno[3,4-b]quinoline cores through gold-catalyzed annulation of anthranils with arenoxyethynes and aryl propargyl ethers

M. D. Patil and R. Liu, Org. Biomol. Chem., 2019, 17, 4452 DOI: 10.1039/C9OB00468H

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