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

Maria I. L. Soares, Clara S. B. Gomes, M. Conceição Oliveira, Joaquim Marçalo, Teresa M. V. D. Pinho e Melo

Research output: Contribution to journalArticlepeer-review

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. This journal is

Original languageEnglish
Pages (from-to)9711-9722
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number44
DOIs
Publication statusPublished - 28 Nov 2021

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