Issue 29, 2023

Microwave-assisted DABCO-promoted regioselective [3 + 3] tandem cyclization: synthesis of pyrrolo[3,4-b]pyridine-4-ones from trifluoromethyl-alkynyl esters and α-aminomaleimide

Abstract

A microwave-assisted DABCO-promoted strategy for the regioselective synthesis of pyrrolo[3,4-b]pyridine-4-one derivatives has been developed from the [3 + 3] annulation of α-aminomaleimide with substituted ethyl 2-butynoate. The characteristic features of this methodology include operational simplicity, high regioselectivity, metal-free reaction conditions, and short reaction times. The potential utility of these methods in biological chemistry and medicinal science applications is highlighted.

Graphical abstract: Microwave-assisted DABCO-promoted regioselective [3 + 3] tandem cyclization: synthesis of pyrrolo[3,4-b]pyridine-4-ones from trifluoromethyl-alkynyl esters and α-aminomaleimide

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2023
Accepted
05 Jul 2023
First published
06 Jul 2023

Org. Biomol. Chem., 2023,21, 6039-6045

Microwave-assisted DABCO-promoted regioselective [3 + 3] tandem cyclization: synthesis of pyrrolo[3,4-b]pyridine-4-ones from trifluoromethyl-alkynyl esters and α-aminomaleimide

Q. Yang, S. Huang, L. Yin, Z. Wang, X. Chen and C. Huang, Org. Biomol. Chem., 2023, 21, 6039 DOI: 10.1039/D3OB01015E

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