scholarly journals Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions

2017 ◽  
Vol 13 ◽  
pp. 54-62 ◽  
Author(s):  
Andreas C Boukis ◽  
Baptiste Monney ◽  
Michael A R Meier
Keyword(s):  
Multicomponent Reactions ◽  
Biginelli Reaction ◽  
2D Nmr ◽  
Solvent System ◽  
Solvent Mixture ◽  
Tandem Reaction ◽  
Reaction Step ◽  
Passerini Reaction ◽  
One Pot ◽  
First Time

The Biginelli reaction was combined with the Passerini reaction for the first time in a sequential multicomponent tandem reaction approach. After evaluation of all possible linker components and a suitable solvent system, highly functionalized dihydropyrimidone–α-acyloxycarboxamide compounds were obtained in good to excellent yields. In a first reaction step, different 3,4-dihydropyrimidin-2(1H)-one acids were synthesized, isolated and fully characterized. These products were subsequently used in a Passerini reaction utilizing a dichloromethane/dimethyl sulfoxide solvent mixture. By variation of the components in both multicomponent reactions, a large number of structurally diverse compounds could be synthesized. In addition, a one-pot Biginelli–Passerini tandem reaction was demonstrated. All products were carefully characterized via 1D and 2D NMR as well as IR and HRMS.

One-pot atom-efficient synthesis of bio-renewable polyesters and cyclic carbonates through tandem catalysis

2015 ◽  
Vol 51 (40) ◽  
pp. 8504-8507 ◽  
Author(s):  
Fan Jia ◽  
Xiaoyu Chen ◽  
Yan Zheng ◽  
Yusheng Qin ◽  
Youhua Tao ◽  
...  
Keyword(s):  
Tandem Reaction ◽  
Cyclic Carbonates ◽  
Tandem Catalysis ◽  
Efficient Synthesis ◽  
One Pot ◽  
One Pot Synthesis ◽  
Salen Complexes ◽  
High Yields ◽  
First Time

One-pot synthesis of well-defined bio-renewable polyesters and cyclic carbonates in high yields was successfully realized for the first time by way of a tandem reaction using metal salen complexes as catalysts.

Uncatalyzed Synthesis of Unsymmetrical Indole-substituted Methane Derivatives via One-pot Multicomponent Reactions under Solvent-free Conditions

2021 ◽  
Vol 18 ◽  
Author(s):  
Shiyin Li ◽  
Xinru Lin ◽  
Xiling Gao ◽  
Wangyu Zeng ◽  
Xiaoyi Wu ◽  
...  
Keyword(s):  
Multicomponent Reactions ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Experimental Results ◽  
Synthetic Method ◽  
One Pot ◽  
Solvent Free Conditions ◽  
First Time

For the first time, one-pot multi-component reactions containing indole, aromatic aldehydes, and dimedone have been achieved in the absence of any catalyst under solvent-free conditions. A class of unsymmetrical indole-substituted methane derivatives and symmetrical diindolylmethanes have been synthesized through this green organic synthetic method. Based on experimental results, a reasonable mechanism for this condensation is emphasized here.

Constructing reduction-sensitive PEGylated NIRF mesoporous silica nanoparticles via a one-pot Passerini reaction for photothermal/chemo-therapy

2018 ◽  
Vol 54 (84) ◽  
pp. 11921-11924 ◽  
Author(s):  
Yu Zhu ◽  
Wenhai Lin ◽  
Xin Wang ◽  
Wei Zhang ◽  
Li Chen ◽  
...  
Keyword(s):  
Mesoporous Silica ◽  
Silica Nanoparticles ◽  
Disulfide Bonds ◽  
Mesoporous Silica Nanoparticles ◽  
Passerini Reaction ◽  
One Pot ◽  
Nirf Imaging ◽  
First Time

For the first time, we have obtained a multifunctional nanoplatform (MSN-BDP-PEG) containing disulfide bonds, BODIPY 5 and PEG-CHO via a one-pot Passerini reaction for chemotherapy, phototherapy and NIRF imaging.

scholarly journals Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones via a Three-Component Biginelli Reaction

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3753
Author(s):  
Giovanna Bosica ◽  
Fiona Cachia ◽  
Riccardo De Nittis ◽  
Nicole Mariotti
Keyword(s):  
Heterogeneous Catalysis ◽  
Calcium Channel ◽  
Calcium Channel Blockers ◽  
Multicomponent Reactions ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Channel Blockers ◽  
Silicotungstic Acid ◽  
One Pot ◽  
Medicinal Properties

Multicomponent reactions are considered to be of increasing importance as time progresses due to the economic and environmental advantages such strategies entail. The three-component Biginelli reaction involves the combination of an aldehyde, a β-ketoester and urea to produce 3,4-dihydropyrimidin-2(1H)-ones, also known as DHPMs. The synthesis of these products is highly important due to their myriad of medicinal properties, amongst them acting as calcium channel blockers and antihypertensive and anti-inflammatory agents. In this study, silicotungstic acid supported on Ambelyst-15 was used as a heterogeneous catalyst for the Biginelli reaction under solventless conditions. Electron-poor aromatic aldehydes gave the best results. Sterically hindered β-ketoesters resulted in lower reaction yields. The reaction was carried out under heterogeneous catalysis to allow easy recovery of the product from the reaction mixture and recycling of the catalyst. The heterogeneity of the reaction was confirmed by carrying out a hot filtration test.

scholarly journals Synthesis and structure revision of symplocin A

2017 ◽  
Vol 4 (6) ◽  
pp. 995-1004 ◽  
Author(s):  
Lu-Ping Shao ◽  
Chang-Mei Si ◽  
Zhuo-Ya Mao ◽  
Wen Zhou ◽  
Tadeusz F. Molinski ◽  
...  
Keyword(s):  
Natural Product ◽  
2D Nmr ◽  
One Pot ◽  
Linear Peptide ◽  
Structure Revision ◽  
First Time

Symplocin A, a linear peptide has been synthesized for the first time employing our previously established ‘one-pot intramolecular tandem protocol’. Moreover, the stereochemistry of natural symplocin A was unambiguously revised through the confirmation by 1D NMR, 2D NMR, and HPLC comparisons with an authentic natural product.

Recent Advances in Biginelli-type Reactions

2020 ◽  
Vol 24 (12) ◽  
pp. 1331-1366
Author(s):  
Majid M. Heravi ◽  
Vahideh Zadsirjan
Keyword(s):  
Multicomponent Reactions ◽  
Medicinal Chemistry ◽  
Biginelli Reaction ◽  
One Pot ◽  
Recent Advances ◽  
Active Methylene Compounds ◽  
Cyclocondensation Reaction ◽  
Biginelli Reactions ◽  
Derivatives Of ◽  
Active Methylene

The effective and high yielding synthesis of poly-functionalized pyrimidines, using multicomponent reactions (MCRs), is imperative in organic and medicinal chemistry. The classic Biginelli reaction is a typically one-pot three-component cyclocondensation reaction involving an aldehyde, a β-ketoester and urea, resulting in the construction of multi-functionalized 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). In recent years, other active methylene compounds, various derivatives of urea and diversely substituted aldehydes have also been used, resulting in the preparation of a new series of various novel dihydropyrimidinones via the Biginelli-Type Reactions (BTRs) or modified Biginelli reactions (MBRs). In this review, we try to underscore the recent advances in BTRs or MBRs.

An Expeditious One-Pot Three-Component Synthesis of 4-Aryl-3,4-dihydrobenzo[g] quinoline-2,5,10(1H)-triones under Green Conditions

2020 ◽  
Vol 23 (23) ◽  
pp. 2626-2634
Author(s):  
Saiedeh Kamalifar ◽  
Hamzeh Kiyani
Keyword(s):  
Reaction Medium ◽  
Meldrum's Acid ◽  
Meldrum’S Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted Benzaldehydes ◽  
High Yields ◽  
First Time ◽  
Green Conditions

: An efficient and facial one-pot synthesis of 4-aryl-3,4-dihydrobenzo[g]quinoline- 2,5,10(1H)-triones was developed for the first time. The process proceeded via the three-component cyclocondensation of 2-amino-1,4-naphthoquinone with Meldrum’s acid and substituted benzaldehydes under green conditions. The fused 3,4-dihydropyridin-2(1H)- one-ring naphthoquinones have been synthesized with good to high yields in refluxing ethanol as a green reaction medium. This protocol is simple and effective as well as does not involve the assistance of the catalyst, additive, or hazardous solvents.

Facile and Efficient Synthesis of New Class of Imidazole Derivatives via One-Pot Multicomponent Reactions in Water

2013 ◽  
Vol 16 (10) ◽  
pp. 788-790
Author(s):  
Zinatossadat Hossaini ◽  
Samereh Seyfi ◽  
Faramarz Rostami-Charati ◽  
Mehdi Ghambarian
Keyword(s):  
Multicomponent Reactions ◽  
Efficient Synthesis ◽  
One Pot ◽  
Imidazole Derivatives ◽  
New Class

1, 1’-Sulfinyldiethylammonium Bis (Hydrogen Sulfate) as a Recyclable Dicationic Ionic Liquid Catalyst for the Efficient Solvent-free Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction

2020 ◽  
Vol 23 (2) ◽  
pp. 157-167
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Dicationic Ionic Liquid

Objective: A facile and efficient method for synthesis of 3, 4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by a novel dicationic Brönsted acidic ionic liquid, [(EtNH2)2SO][HSO4]2, has been successfully developed. Material and Method:: 3, 4-Dihydropyrimidin-2(1H)-ones were synthesized through one-pot condensation of aromatic aldehydes, ethyl acetoacetate, and urea under solvent-free conditions using [(EtNH2)2SO][HSO4]2 as a novel catalyst. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate / n-hexane = 1 / 5). The products have been characterized by IR, 1H NMR, 13C NMR, and also by their melting points. Results: In this research, a library of dihydropyrimidinone derivatives was synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as a catalyst. Various aromatic aldehydes, as well as heteroaromatic aldehydes, were employed, affording good to high yields of the corresponding products and illustrating the substrate generality of the present method. In addition, the prepared dicationic Brönsted acidic ionic liquid can be easily recovered and reused. Conclusion: 1, 1’-Sulfinyldiethylammonium bis (hydrogen sulfate), as a novel dicationic ionic liquid, can act as a highly efficient catalyst for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions.

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