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Keywords = Biginelli and Hantzsch multicomponent reactions

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20 pages, 4832 KiB  
Review
Green Catalysts and/or Green Solvents for Sustainable Multi-Component Reactions
by Gatien Messire, Emma Caillet and Sabine Berteina-Raboin
Catalysts 2024, 14(9), 593; https://doi.org/10.3390/catal14090593 - 4 Sep 2024
Cited by 8 | Viewed by 3769
Abstract
Here, we describe some well-known multicomponent reactions and the progress made over the past decade to make these processes even more environmentally friendly. We focus on the Mannich, Hantzsch, Biginelli, Ugi, Passerini, Petasis, and Groebke–Blackburn–Bienaymé reactions. After describing the origin of the reactions [...] Read more.
Here, we describe some well-known multicomponent reactions and the progress made over the past decade to make these processes even more environmentally friendly. We focus on the Mannich, Hantzsch, Biginelli, Ugi, Passerini, Petasis, and Groebke–Blackburn–Bienaymé reactions. After describing the origin of the reactions and their mechanisms, we summarize some advances in terms of the eco-compatibility of these different MCRs. These are followed by examples of some reactions, considered as variants, which are less well documented but which are promising in terms of structures generated or synthetic routes. Full article
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17 pages, 5315 KiB  
Article
Multicomponent Reactions Promoted by Ecocatalyst from Metal Hyperaccumulating Plant Pluchea sagittalis
by Leonardo H. R. Alponti, Monize Picinini, Ernesto A. Urquieta-Gonzalez, Caroline S. da Silva, Simone Y. S. Silva, Sebastião C. Silva, Marilene N. de Oliveira, Juliana Viera, Maria Fatima das G. F. da Silva and Arlene G. Corrêa
Reactions 2023, 4(4), 552-568; https://doi.org/10.3390/reactions4040033 - 7 Oct 2023
Viewed by 1906
Abstract
Phytoremediation has been considered a sustainable environmental technology for heavy metals decontamination. In this work, we evaluated the metal contents by inductively coupled plasma optical emission spectrometry (ICP-OES) of three plant species collected in a mine in the Brazilian Amazonia area. Based on [...] Read more.
Phytoremediation has been considered a sustainable environmental technology for heavy metals decontamination. In this work, we evaluated the metal contents by inductively coupled plasma optical emission spectrometry (ICP-OES) of three plant species collected in a mine in the Brazilian Amazonia area. Based on this analysis, Pluchea sagitallis leaves were selected to prepare metallic ecocatalysts. The leaf ashes and the obtained ecocatalysts were characterized by ICP-OES, X-ray diffraction (XRD), scanning electron microscopy (SEM) and N2-physisorption measurements. Moreover, they were evaluated in the Biginelli and Hantzsch multicomponent reactions, furnishing the corresponding 3,4-dihydropyrimidin-2-(1H)-ones and 1,4-dihydropyridines with good to excellent yields. The best ecocatalyst was easily recovered and recycled in up to six reactions without a significant decrease in its performance. Full article
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13 pages, 221 KiB  
Article
Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters
by Joel Martínez, Stephany Romero-Vega, Rita Abeja-Cruz, Cecilio Álvarez-Toledano and René Miranda
Int. J. Mol. Sci. 2013, 14(2), 2903-2915; https://doi.org/10.3390/ijms14022903 - 30 Jan 2013
Cited by 30 | Viewed by 6441
Abstract
Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-dihydropyrimidinones, derived from formylphenylboronic acids (ortho [...] Read more.
Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-dihydropyrimidinones, derived from formylphenylboronic acids (ortho, meta and para), were obtained using a green approach, involving H-4CR and B-3CR practices, in the presence of ethanol, which is a green solvent, and using three comparatively different modes of activation (mantle heating, yield 3%–7% in 24 h, Infrared Radiation (IR) irradiation, yield 12%–17% in 12 h, and microwave irradiation, yield 18%–80%, requiring very low reaction times of 0.25–0.33 h). In addition, as a green-approach is offered, a convenient analysis, of the 12 green chemistry principles for the overall procedure was performed. Finally, since all the products are new, characterizations were carried out using common analytic procedures (1H, 11B, and 13C NMR, FAB+MS, HRMS, and IR). The accurate mass data of unexpected ions related to interactions between thioglycerol and the expected products, in the FAB+-mode, enabled unequivocal characterization of the target molecules. Full article
(This article belongs to the Section Green Chemistry)
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8 pages, 83 KiB  
Article
Sulfated Zirconia-Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) Under Solventless Conditions: Competitive Multicomponent Biginelli vs. Hantzsch Reactions
by Deyanira Angeles-Beltrán, Leticia Lomas-Romero, Victor H. Lara-Corona, Eduardo González-Zamora and Guillermo Negrón-Silva
Molecules 2006, 11(10), 731-738; https://doi.org/10.3390/11100731 - 2 Oct 2006
Cited by 47 | Viewed by 11618
Abstract
The catalytic ability of ZrO2/SO42- to promote solventless three-componentcondensation reactions of a diversity of aromatic aldehydes, urea or thoiurea and ethylacetoacetate was studied. Products resulting from Hantzsch and/or Biginelli multi-component reactions are obtained in the presence of solid acid [...] Read more.
The catalytic ability of ZrO2/SO42- to promote solventless three-componentcondensation reactions of a diversity of aromatic aldehydes, urea or thoiurea and ethylacetoacetate was studied. Products resulting from Hantzsch and/or Biginelli multi-component reactions are obtained in the presence of solid acid catalysts using the samereactants but different temperature conditions. The sulfated zirconia catalyst can berecovered and recycled in subsequent reactions with a gradual decrease of activity. Full article
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