scholarly journals Ethyl 6-Methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Molbank ◽  
10.3390/m1076 ◽  
2019 ◽  
Vol 2019 (3) ◽  
pp. M1076
Author(s):  
Gonçalves ◽  
Azambuja ◽  
Davi ◽  
Gonçalves ◽  
Kagami ◽  
...  
Keyword(s):  
Active Compound ◽  
Biginelli Reaction ◽  
Dipolar Cycloaddition ◽  
Three Component Reaction ◽  
Acid Catalyzed

The Biginelli reaction is an acid-catalyzed, three-component reaction between an aldehyde, a hydrogen methylene active compound, and urea (or its analogue) and constitutes a rapid and easy synthesis of highly functionalized heterocycles. Synthesis of ethyl 6-methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate, identified by our laboratory code LaSOM® 293, was achieved using the Biginelli reaction as the key step, followed by the Huisgen 1,3-dipolar cycloaddition in a convergent four-step route. The product LaSOM® 293 was obtained with a yield of 84%.

Ascorbic acid-Catalyzed One-Pot Three-Component Biginelli Reaction: A Practical and Green Approach towards Synthesis of 3,4-dihydropyrimidin- 2(1H)-ones/thiones

2013 ◽  
Vol 10 (7) ◽  
pp. 463-467 ◽  
Author(s):  
Imene Sehout ◽  
Raouf Boulcina ◽  
Boudjemaa Boumoud ◽  
Fabienne Berree ◽  
Bertrand Carboni ◽  
...  
Keyword(s):  
Ascorbic Acid ◽  
Biginelli Reaction ◽  
One Pot ◽  
Green Approach ◽  
Acid Catalyzed

Synthesis of 1,3,4-trisubstituted pyrrolidines as meropenem adjuvants targeting New Delhi metallo-β-lactamase

2021 ◽  
Vol 45 (7) ◽  
pp. 3515-3534
Author(s):  
Wen Bin Jin ◽  
Chen Xu ◽  
Xiao Lin Qi ◽  
Ping Zeng ◽  
Wei Gao ◽  
...  
Keyword(s):  
Boric Acid ◽  
Dipolar Cycloaddition ◽  
New Delhi ◽  
Acid Catalyzed

A promising NDM-1 inhibitor was discovered by the construction of pyrrolidine library via boric acid-catalyzed 1,3-dipolar cycloaddition and cell-based screens.

scholarly journals Diastereoselective synthesis of dispirooxindoles via [3+2] cycloaddition of azomethine ylides to 3-phenacylideneoxindoles and evaluation of their cytotoxicity

RSC Advances ◽  
2018 ◽  
Vol 8 (42) ◽  
pp. 23990-23995 ◽  
Author(s):  
Ying Huang ◽  
Yi-Xin Huang ◽  
Jing Sun ◽  
Chao-Guo Yan
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
Three Component Reaction

The three-component reaction of 1,2,3,4-tetrahydroisoquinoline, isatins and 3-phenacylideneoxindoles in refluxing ethanol afforded dispiro[indoline-3,1′-pyrrolo[2,1-a]isoquinoline-3′,3′-indolines] (4a–4x) in good yields via 1,3-dipolar cycloaddition.

Three-component 3-(phosphoryl)methylindole synthesis from indoles, H-phosphine oxides and carbonyl compounds under metal-free conditions

2019 ◽  
Vol 21 (4) ◽  
pp. 792-797 ◽  
Author(s):  
Jiaoting Pan ◽  
Runmin Zhao ◽  
Jiami Guo ◽  
Dumei Ma ◽  
Ying Xia ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Indole Derivatives ◽  
Phosphine Oxides ◽  
One Pot ◽  
Metal Free ◽  
Three Component Reaction ◽  
Acid Catalyzed

The first facile and efficient acid-catalyzed three-component reaction of indoles, H-phosphine oxides and carbonyl compounds has been developed, providing a general, one-pot approach to structurally diverse C3-alkylated indole derivatives.

scholarly journals A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles

2019 ◽  
Vol 15 ◽  
pp. 1061-1064 ◽  
Author(s):  
Alexei Lukin ◽  
Anna Bakholdina ◽  
Anna Kryukova ◽  
Alexander Sapegin ◽  
Mikhail Krasavin
Keyword(s):  
Lewis Acid ◽  
Primary Amine ◽  
Three Component Reaction ◽  
Acid Catalyzed ◽  
In Situ Generation

A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported base-promoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

Lewis Acid-Catalyzed Intermolecular Annulation: Three-Component Reaction toward Imidazo[1,2-a]pyridine Thiones

2019 ◽  
Vol 84 (14) ◽  
pp. 9369-9377 ◽  
Author(s):  
Zhengwang Chen ◽  
Pei Liang ◽  
Fan Xu ◽  
Rulin Qiu ◽  
Qi Tan ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Three Component Reaction ◽  
Acid Catalyzed

Efficient Synthesis 2,3-Dihydroquinazolin-4(1H)-Ones Using Coconut Shell Char Sulfonic Acid as a Reusable Catalyst in Ethanol

2014 ◽  
Vol 989-994 ◽  
pp. 83-86
Author(s):  
Xuan Yan Liu ◽  
Zhi Gao Yang
Keyword(s):  
Sulfonic Acid ◽  
Biginelli Reaction ◽  
Acid Catalyst ◽  
Coconut Shell ◽  
Reusable Catalyst ◽  
Efficient Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Three Component Reaction ◽  
High Yields

3,4-Dihydropyrimidin-2(1H)-ones derivatives were synthesized in moderate to high yields in one-pot three component reaction from the corresponding aldehydes, 1,3-dicarbonyl compounds and urea, Coconut shell char sulfonic acid (CSCSA) used as a reusable, and efficient catalyst. Compared to the classical acid catalyst, This new protocol for the Biginelli reaction includes the following important features: excellent yields, non-toxic, inexpensive and easily available reagent.

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