Acid-Catalyzed 1,3-Dipolar Cycloaddition of 2H-Azirines with Nitrones: An Unexpected Access to 1,2,4,5-Tetrasubstituted Imidazoles

2020 ◽  
Vol 85 (5) ◽  
pp. 3587-3595 ◽  
Author(s):  
Anikó Angyal ◽  
András Demjén ◽  
János Wölfling ◽  
László G. Puskás ◽  
Iván Kanizsai
Keyword(s):  
Dipolar Cycloaddition ◽  
Acid Catalyzed ◽  
Tetrasubstituted Imidazoles

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.

ChemInform Abstract: Iron- and Ruthenium-Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions Between Enals and Diaryl Nitrones.

ChemInform ◽  
2009 ◽  
Vol 40 (1) ◽  
Author(s):  
Andrei Badoiu ◽  
Gerald Bernardinelli ◽  
Jiri Mareda ◽  
E. Peter Kuendig ◽  
Florian Viton
Keyword(s):  
Lewis Acid ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Acid Catalyzed

ChemInform Abstract: Chiral Phosphoric Acid Catalyzed Enantioselective 1,3-Dipolar Cycloaddition Reaction of Azlactones.

ChemInform ◽  
2016 ◽  
Vol 47 (21) ◽  
Author(s):  
Zhenhua Zhang ◽  
Wangsheng Sun ◽  
Gongming Zhu ◽  
Junxian Yang ◽  
Ming Zhang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

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%.

Iron- and Ruthenium-Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions between Enals and Diaryl Nitrones

2008 ◽  
Vol 3 (8-9) ◽  
pp. 1298-1311 ◽  
Author(s):  
Andrei Bădoiu ◽  
Gerald Bernardinelli ◽  
Jiri Mareda ◽  
E. Peter Kündig ◽  
Florian Viton
Keyword(s):  
Lewis Acid ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Acid Catalyzed

scholarly journals Iron- and Ruthenium-Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions between Enals and Diaryl Nitrones

2009 ◽  
Vol 4 (7) ◽  
pp. 1021-1022 ◽  
Author(s):  
Andrei Bădoiu ◽  
Gerald Bernardinelli ◽  
Jiri Mareda ◽  
E. Peter Kündig ◽  
Florian Viton
Keyword(s):  
Lewis Acid ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Acid Catalyzed

Chiral phosphoric acid catalyzed enantioselective 1,3-dipolar cycloaddition reaction of azlactones

2016 ◽  
Vol 52 (7) ◽  
pp. 1377-1380 ◽  
Author(s):  
Zhenhua Zhang ◽  
Wangsheng Sun ◽  
Gongming Zhu ◽  
Junxian Yang ◽  
Ming Zhang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

The first chiral phosphoric acid catalyzed highly diastereo- and enantioselective 1,3-dipolar cycloaddition reaction of azlactones and methyleneindolinones was disclosed to yield 3,3′-pyrrolidonyl spirooxindole scaffolds.

Lewis Acid Catalyzed Regio- and Diastereoselective Synthesis of Spiroisoxazolines via One-Pot Sequential Knoevenagel Condensation/1,3-Dipolar Cycloaddition Reaction

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1669-1679 ◽  
Author(s):  
Ayoob Bazgir ◽  
Hossein Yazdani
Keyword(s):  
Knoevenagel Condensation ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Coupling Reactions ◽  
Diastereoselective Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Ch Acids ◽  
Acid Catalyzed ◽  
Metal Catalyzed

A ZnCl2-catalyzed regio- and diastereoselective one-pot sequential Knoevenagel condensation/1,3-dipolar cycloaddition reaction of CH acids (oxindole, 1,3-indandione, and 3H-pyrazol-3-one), aldehydes, and dibromoformaldoxime has been established. The method allows the synthesis of diversely functionalized spiroisoxazolines in good isolated yields under mild reaction conditions. Moreover, the preparation of spiroindene-isoxazole-1,3-diones containing benzoimidazole or benzothiazole moieties as new ligands for the metal-catalyzed coupling reactions and C–H activation is demonstrated.

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