Synthesis of 5-Aryloxazolidines via 1,3-Dipolar Cycloaddition Reaction of a Non-Stabilized Azomethine Ylide with Aromatic Aldehydes

2007 ◽  
Vol 60 (12) ◽  
pp. 898 ◽  
Author(s):  
John H. Ryan ◽  
Nadia Spiccia ◽  
Leon S.-M. Wong ◽  
Andrew B. Holmes
Keyword(s):  
Trifluoroacetic Acid ◽  
Cycloaddition Reaction ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition

The 1,3-dipolar cycloaddition reaction of a non-stabilized azomethine ylide 4a, formed in situ from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine 5 and a catalytic amount of trifluoroacetic acid, with aromatic aldehydes 3 gives rise to N-benzyl-5-aryloxazolidines 1. Under these conditions, 4-hydroxybenzaldehyde 3p undergoes two-fold addition of azomethine ylide 4a to afford bis adduct 11.

ChemInform Abstract: Synthesis of 5-Aryloxazolidines via 1,3-Dipolar Cycloaddition Reaction of a Non-Stabilized Azomethine Ylide with Aromatic Aldehydes.

ChemInform ◽  
2008 ◽  
Vol 39 (22) ◽  
Author(s):  
John H. Ryan ◽  
Nadia Spiccia ◽  
Leon S.-M. Wong ◽  
Andrew B. Holmes
Keyword(s):  
Cycloaddition Reaction ◽  
Aromatic Aldehydes ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition

scholarly journals Diastereoselective Synthesis of Spiro[Pyrrolo[2,1-B][1,3] Benzothiazole-3,5′-[1,3]Thiazolo[3,2-B][1,2,4]Triazol]-6′-Ones via Cycloaddition Reaction of Benzothiazolium Salts

2018 ◽  
Vol 42 (7) ◽  
pp. 371-373 ◽  
Author(s):  
Qing Zeng ◽  
Demin Ren ◽  
Yulin Huang ◽  
Xinliang Fu ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of (Z)-5-arylidene[1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-one and azomethine ylide, which was generated in situ by the reaction of N-4-methoxyphenacylbenzothiazolium bromides and triethylamine, afforded novel 2-(aryl)-1-(4-methoxybenzoyl)-1,2-dihydrospiro[pyrrolo[2,1-b][1,3]benzothiazole-3,5′-[1,3]thiazolo[3,2-b][1,2,4]triazol]-6′-ones in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS spectroscopy together with X-ray crystallographic analysis.

scholarly journals Synthesis of Dispiro[Indeno[1,2-b]Quinoxaline-11,3′-Pyrrolizine-2′,2″-[1,3] Thiazolo[3,2-a]Pyrimidine Via Cycloaddition Reactions

2018 ◽  
Vol 42 (9) ◽  
pp. 453-455 ◽  
Author(s):  
Demin Ren ◽  
Xiaolian Hu ◽  
Yulin Huang ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of ethyl 5-aryl-2-(2-methoxy-2-oxoethylidene)-7-methyl-3-oxo-2,3-dihydro-5 H-[1,3]thiazolo[3,2- a] pyrimidine-6-carboxylate and azomethine ylide, which was generated in situ by the reaction of 11 H-indeno[1,2- b]quinoxalin-11-one and L-proline, afforded novel 6″ethyl 1′-methyl 5″aryl-7″methyl-3″oxo-5’,6’,7’,7a′-tetrahydro-1' H,3″ H,5″ H-dispiro[indeno[1,2- b]quinoxaline-11, 3 ‘-pyrrolizine-2’,2″-[1,3]thiazolo[3,2- a]pyrimidine-1’,6″-dicarboxylates in good yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS together with X-ray crystallographic analysis.

Synthesis of Spiro[Pyrrolo[2,1-b][1,3]Benzothiazole-3,2′-[1,3]Thiazolo[3,2-a] Pyrimidine] via Cycloaddition Reactions

2018 ◽  
Vol 42 (5) ◽  
pp. 260-263 ◽  
Author(s):  
Qing Zeng ◽  
Demin Ren ◽  
Xingliang Fu ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of ethyl-5-aryl-2-[( Z)-2-methoxy-2-oxoethylidene]-7-methyl-3-oxo-3,5-dihydro-2 H-thiazolo[3,2- a] pyrimidine-6-carboxylates and azomethine ylide, which was generated in situ by the reaction of N-4-methoxyphenacylbenzothiazolium bromides and triethylamine, yielded novel 6′-ethyl-2-methyl-5′-aryl-1-(4-methoxybenzoyl)-7-methyl-3′-oxo-1,2-dihydro-5 H-spiro[pyrrolo[2,1- b][1,3]benzothiazole-3,2′-[1,3]thiazolo[3,2- a]pyrimidine]-2,6′-dicarboxylates in moderate yields. The structures of all of the products were characterised by NMR, IR, HRMS spectrometry, together with X-ray crystallographic analysis.

scholarly journals [Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids

Molecules ◽  
2020 ◽  
Vol 25 (20) ◽  
pp. 4779 ◽  
Author(s):  
Raju Suresh Kumar ◽  
Dhaifallah M. Al-thamili ◽  
Abdulrahman I. Almansour ◽  
Natarajan Arumugam ◽  
Necmi Dege
Keyword(s):  
Reaction Rate ◽  
Cycloaddition Reaction ◽  
Reaction Medium ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Synthetic Approach ◽  
One Pot ◽  
Short Reaction Time ◽  
Phenyl Alanine

Our synthetic approach for the assembly of structurally complex spirooxindole heterocyclic hybrids was based on an ionic liquid, [bmim]Br mediated one-pot three-component cascade reaction strategy involving 1,3-dipolar cycloaddition reaction of N-1-(2-pyridinylmethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones and azomethine ylide generated in situ from isatin and L-phenyl alanine, affording a series of spirooxindole–pyrrolidine heterocyclic hybrids in good-to-excellent yields. In addition to serving as the reaction medium, [bmim]Br also functioned as a catalyst in this cycloaddition reaction and hence accelerated the reaction rate affording the cycloadducts in short reaction time.

scholarly journals Ultrasound-assisted, ZnBr2-catalyzed regio- and stereoselective synthesis of novel 3,3′-dispiropyrrolidine bisoxindole derivatives via 1,3-dipolar cycloaddition reaction of an azomethine ylide

ARKIVOC ◽  
2017 ◽  
Vol 2017 (5) ◽  
pp. 20-31 ◽  
Author(s):  
Mostafa Kiamehr ◽  
Mohammad R. Khodabakhshi ◽  
Firouz M. Moghaddam ◽  
Alexander Villinger ◽  
Peter Langer
Keyword(s):  
Stereoselective Synthesis ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Ultrasound Assisted

scholarly journals Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

Asymmetric, stereocontrolled total synthesis of (+) and (−)-spirotryprostatin B via a diastereoselective azomethine ylide [1,3]-dipolar cycloaddition reaction

Tetrahedron ◽  
2002 ◽  
Vol 58 (32) ◽  
pp. 6311-6322 ◽  
Author(s):  
Paul R Sebahar ◽  
Hiroyuki Osada ◽  
Takeo Usui ◽  
Robert M Williams
Keyword(s):  
Total Synthesis ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition

Catecholated graphene-filled polyimide with enhanced mechanical, thermal, and tribological properties

2020 ◽  
pp. 095400832094035
Author(s):  
Xing Wu ◽  
Zhengyu Jin ◽  
Yuejin Zhu ◽  
Haichao Zhao
Keyword(s):  
Friction And Wear ◽  
In Situ Polymerization ◽  
Cycloaddition Reaction ◽  
Mechanical Analysis ◽  
Dipolar Cycloaddition ◽  
Wear Properties ◽  
Comprehensive Properties ◽  
Transmission Electron ◽  
Friction And Wear Tests

In order to achieve good dispersion of graphene in polyimide (PI), catecholated graphene (G-Cat) was prepared by 1,3-dipolar cycloaddition reaction of N-methylglycine and 3,4-dihydroxybenzaldehyde with graphene sheets. G-Cat/PI composites were prepared by in situ polymerization with pyromellitic dianhydride and 4,4-oxydianiline in the presence of G-Cat. The successful modification of graphene was proved by infrared spectroscopy, Raman spectroscopy, and transmission electron microscopy. The comprehensive properties of G-Cat/PI composites were studied by tensile, dynamic mechanical analysis, thermogravimetric analysis, and friction and wear tests. By observing the morphology of wear marks, the friction and wear properties of the composites were emphatically analyzed. Therefore, graphene/PI composites were expected to have broad application prospects in lubrication and wear resistance.

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