Issue 44, 2021

Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates

Abstract

The DABCO-catalyzed [3 + 3] annulation between 3-nitro-2H-chromenes and benzyl 2,3-butadienoate has been developed as a route to 5H-chromeno[3,4-b]pyridine derivatives. Under optimal reaction conditions, 5H-chromeno[3,4-b]pyridines incorporating two allenoate units were obtained in moderate to good yields (30–76%). The same type of transformation could be carried out using butynoates as allene surrogates. Mechanistic studies by mass spectrometry allowed the identification of the key intermediates involved in the reaction mechanism. The reported synthetic methodology represents an entirely new approach for the synthesis of the 5H-chromeno[3,4-b]pyridine core structure based on allene chemistry.

Graphical abstract: Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates

Supplementary files

Article information

Article type
Paper
Submitted
11 Jun 2021
Accepted
22 Oct 2021
First published
26 Oct 2021

Org. Biomol. Chem., 2021,19, 9711-9722

Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates

M. I. L. Soares, C. S. B. Gomes, M. C. Oliveira, J. Marçalo and T. M. V. D. Pinho e Melo, Org. Biomol. Chem., 2021, 19, 9711 DOI: 10.1039/D1OB01130H

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