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Synthesis 2021; 53(02): 365-370
DOI: 10.1055/s-0040-1706422
paper
© Georg Thieme Verlag Stuttgart · New York

A Domino Reaction for the Synthesis of Novel 1,3-Dihydrofuro[3,4-c]pyridines from Pyridoxal and Ketones

Izamara Casadia
a   Grupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul (Laboratório 1), Universidade Federal da Grande Dourados, 79804-970, Dourados-MS, Brazil   Email: lucas.pizzuti@gmail.com
,
Thalita O. Daher
a   Grupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul (Laboratório 1), Universidade Federal da Grande Dourados, 79804-970, Dourados-MS, Brazil   Email: lucas.pizzuti@gmail.com
,
Sidnei Moura
b   Laboratório de Biotecnologia de Produtos Naturais e Sintéticos, Universidade de Caxias do Sul, 95070-560, Caxias do Sul-RS, Brazil
,
Davi F. Back
c   Laboratório de Materiais Inorgânicos, Universidade Federal de Santa Maria, 97105-900, Santa Maria-RS, Brazil
,
Eliandro Faoro
a   Grupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul (Laboratório 1), Universidade Federal da Grande Dourados, 79804-970, Dourados-MS, Brazil   Email: lucas.pizzuti@gmail.com
,
Cristiane S. Schwalm
a   Grupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul (Laboratório 1), Universidade Federal da Grande Dourados, 79804-970, Dourados-MS, Brazil   Email: lucas.pizzuti@gmail.com
,
Gleison A. Casagrande
a   Grupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul (Laboratório 1), Universidade Federal da Grande Dourados, 79804-970, Dourados-MS, Brazil   Email: lucas.pizzuti@gmail.com
,
Guilherme C. Paveglio
a   Grupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul (Laboratório 1), Universidade Federal da Grande Dourados, 79804-970, Dourados-MS, Brazil   Email: lucas.pizzuti@gmail.com
,
Lucas Pizzuti  ∗
a   Grupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul (Laboratório 1), Universidade Federal da Grande Dourados, 79804-970, Dourados-MS, Brazil   Email: lucas.pizzuti@gmail.com
› Author AffiliationsThis work was supported by Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, grant number 435178/2018-0).
Further Information

Publication History

Received: 28 June 2020

Accepted after revision: 20 July 2020

Publication Date:
20 August 2020 (online)

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Abstract

A convenient domino route for the synthesis of novel 1,3-dihydrofuro[3,4-c]pyridines from pyridoxal and alkyl, aryl or heteroaryl ketones under basic conditions is reported. A series of nine derivatives is obtained in 53–90% yields after stirring reactants for 48 hours at room temperature. Most products are easily isolated by filtration followed by recrystallization from ethanol. All products were fully characterized by FTIR, HRMS, and 1H and 13C NMR spectroscopy. The X-ray crystal structure of a representative example of the 1,3-dihydrofuro[3,4-c]pyridine series is also presented.

Key words

biobased molecules - Claisen–Schmidt condensation - domino reactions - fused-ring systems - oxa-Michael addition - vitamins

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706422.
  • Supporting Information
 

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