Green Synthesis of Hantzsch Dihydropyridines from Biorenewable Furans Derived from Lignocellulosic Biomass

Hantzsch dihydropyridines constitute a class of N‐heterocycles with significant pharmacological and technological applications. Due to their importance, the development of new sustainable synthetic methodologies for producing dihydropyridines is of great interest. This work presents the synthesis of dihydropyridines via the Hantzsch multicomponent reaction. Furanic aldehydes derived from lignocellulosic biomass are used as substrates, and p ‐sulfonic acid calix[4]arene (CX4SO 3 H) is employed as an organocatalyst, under microwave irradiation (MWI). The furanic compounds are reacted with ethyl acetoacetate and ammonium acetate in the presence of 1.0 mol% of CX4SO 3 H for 10 min at 80 °C under MWI. Twenty one dihydropyridines are synthesized in yields ranging from 43% to 96%. Two dihydropyridines are obtained as crystals suitable for X‐ray diffraction analysis, and their crystallographic data are provided. Moreover, the catalytic system can be reused for seven reaction cycles without significant yield loss. The developed methodology offers numerous advantages. It enables the production of dihydropyridines from renewable substrates via a multicomponent reaction in a single step, with a short reaction time. The process uses a reusable organocatalyst and eliminates the need for solvents or metal catalysts.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-06-27
DOI
https://doi.org/10.1002/ejoc.202500278
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
0.00

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article

Green Synthesis of Hantzsch Dihydropyridines from Biorenewable Furans Derived from Lignocellulosic Biomass

Paula Derksen Macruz, Gabriel Abranches Dias Castro, Eduardo Jorge Pilau, Felipe Terra Martins et al.
European Journal of Organic Chemistry
Multicomponent Synthesis of Heterocycles
article

Green Synthesis of Hantzsch Dihydropyridines from Biorenewable Furans Derived from Lignocellulosic Biomass

Paula Derksen Macruz, Gabriel Abranches Dias Castro, Eduardo Jorge Pilau, Felipe Terra Martins, Sérgio Antônio Fernandes, Eduardo Vinícius Vieira Varejão, Lorena Cristina de Andrade Leles
article en

Abstract

Hantzsch dihydropyridines constitute a class of N‐heterocycles with significant pharmacological and technological applications. Due to their importance, the development of new sustainable synthetic methodologies for producing dihydropyridines is of great interest. This work presents the synthesis of dihydropyridines via the Hantzsch multicomponent reaction. Furanic aldehydes derived from lignocellulosic biomass are used as substrates, and p ‐sulfonic acid calix[4]arene (CX4SO 3 H) is employed as an organocatalyst, under microwave irradiation (MWI). The furanic compounds are reacted with ethyl acetoacetate and ammonium acetate in the presence of 1.0 mol% of CX4SO 3 H for 10 min at 80 °C under MWI. Twenty one dihydropyridines are synthesized in yields ranging from 43% to 96%. Two dihydropyridines are obtained as crystals suitable for X‐ray diffraction analysis, and their crystallographic data are provided. Moreover, the catalytic system can be reused for seven reaction cycles without significant yield loss. The developed methodology offers numerous advantages. It enables the production of dihydropyridines from renewable substrates via a multicomponent reaction in a single step, with a short reaction time. The process uses a reusable organocatalyst and eliminates the need for solvents or metal catalysts.

European Journal of Organic ChemistryVol. 28(28)
Universidade Estadual de Maringá (BR), Universidade Federal de Viçosa (BR), Universidade Federal de Goiás (BR)
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico, Financiadora de Estudos e Projetos, Fundação de Amparo à Pesquisa do Estado de Minas Gerais
Openalex Percentile: Top 89%
Multicomponent Synthesis of Heterocycles
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