1,3-Dipolar cycloadditions of N-(5-nitro-2-furfuryl)isoquinolinium bromide in the synthesis of benzoindolizines

1984 ◽  
Vol 49 (2) ◽  
pp. 533-542 ◽  
Author(s):  
Jarmila Štetinová ◽  
Jaroslav Kováč ◽  
František Považanec ◽  
Miloslava Dandárová ◽  
Alžbeta Pajchortová
Keyword(s):  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Spectral Evidence

Substituted 3-(5-nitro-2-furyl)benzo[g]indolizines III-XII were synthesized by a 1,3-dipolar cycloaddition of the ylide II formed in situ from N-(5-nitro-2-furfuryl)isoquinolinium bromide (I) and dimethyl butinedioate, diethyl butenedioate, 1-nitro-2-phenylethylene, ethyl 2-propenoate, ethyl 3-(5-nitro-2-furyl)-2-propenoate, 1,3-diphenyl-2-propenone, 1,3-diphenyl-2-propinone, 2-propenenitrile, 1-phenyl-3-(5-nitro-2-furyl)-2-propenone, and methyl 2-cyano-3-(4-nitrophenyl)-2-propenoate. Structure of these products was verified by spectral evidence.

Cross 1,3-dipolar cycloadditions of C,N-cyclic azomethine imines with an N-benzyl azomethine ylide: facile access to fused tricyclic 1,2,4-hexahydrotriazines

2019 ◽  
Vol 17 (2) ◽  
pp. 244-247 ◽  
Author(s):  
Kai-Kai Wang ◽  
Yan-Li Li ◽  
Zhan-Yong Wang ◽  
Meng-Wei Hu ◽  
Ting-Ting Qiu ◽  
...  
Keyword(s):  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Azomethine Imines

A cross 1,3-dipolar cycloaddition of two different ylides between C,N-cyclic azomethine imines with an in situ generated non-stabilized azomethine ylide from an N-benzyl precursor is reported.

scholarly journals Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

2019 ◽  
Vol 91 (4) ◽  
pp. 575-596 ◽  
Author(s):  
Carmen Nájera ◽  
José Miguel Sansano
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives ◽  
Reaction Conditions ◽  
Dipolar Cycloadditions ◽  
Spiro Derivatives ◽  
Stabilized Azomethine Ylides

Abstract Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic α-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.

Synthesis of isoxazole conjugates of sugars via 1,3-dipolar cycloaddition

2008 ◽  
Vol 86 (2) ◽  
pp. 138-141 ◽  
Author(s):  
Vipraja V Vaidya ◽  
Karuna S Wankhede ◽  
Manikrao M Salunkhe ◽  
Girish K Trivedi
Keyword(s):  
Click Chemistry ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
High Degree

Isoxazole conjugates of sugar have been synthesized by the aid of 1,3-dipolar cycloaddition in a click chemistry approach. The sugar-derived propargyl ethers underwent 1,3-dipolar cycloadditions smoothly with in situ generated nitrile oxides from aromatic oximes in good yields. The reaction exhibited a high degree of regioselectivity.Key words: isoxazole conjugates, 1,3-dipolar cycloadditions, nitrile oxides.

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

1,3-Dipolar cycloadditions of Arylcarbonitrile Oxides and Diaryl Nitrilimines with Some 2-Arylmethylene-1,3-Indanediones; regiochemistry of the Reactions

2003 ◽  
Vol 2003 (4) ◽  
pp. 204-207 ◽  
Author(s):  
Sarra Boudriga ◽  
Mohiedinne Askri ◽  
Rafik Gharbi ◽  
Mohamed Rammah ◽  
Kabula Ciamala
Keyword(s):  
Ring Closure ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions

Ring-closure reaction affording spiroisoxazolines and spiropyrazolines via a 1,3-dipolar cycloaddition between the title compounds, occurs with high regioselectivity.

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.

Regioselection in 1,3-Dipolar Cycloadditions of 3-Methylpyridine N-Imide to Aromatic Carbonitriles. Synthesis of 2-Aryl-8-Methyl[1,2,4]Triazolo [1,5-a]Pyridines

2002 ◽  
Vol 2002 (11) ◽  
pp. 560-561 ◽  
Author(s):  
Zhang Guolin ◽  
Hu Yongzhou
Keyword(s):  
Potassium Hydroxide ◽  
Dipolar Cycloaddition ◽  
Aromatic Nitriles ◽  
Dipolar Cycloadditions

1-Amino-3-methylpyridinium mesitylenesulfonate (3) reacts with aromatic nitriles in the presence of potassium hydroxide, undergoing 1,3-dipolar cycloaddition followed by elimination of H2 to give 2-aryl-8-methyl[1,2,4]triazolo[1,5- a]pyridines as the major products, rather than the 6-methyl isomers.

Asymmetric 1,3-Dipolar Cycloaddition of Nitrile Oxides Generated in situ by Direct Oxidation of Aldoximes

2002 ◽  
Vol 31 (11) ◽  
pp. 1112-1113 ◽  
Author(s):  
Masamichi Tsuji ◽  
Yutaka Ukaji ◽  
Katsuhiko Inomata
Keyword(s):  
Dipolar Cycloaddition ◽  
Direct Oxidation ◽  
Nitrile Oxides

scholarly journals Synthesis of Aza-Pterocarpan Analogues via 1,3 Intramolecular Dipolar Cycloadditions in in situ generated Iminoolefins

2013 ◽  
Author(s):  
Julio C.F.Barcellos ◽  
Ayres G. Dias ◽  
José M. Sansano ◽  
Carmen Nájera ◽  
Paulo R. R. Costa
Keyword(s):  
Dipolar Cycloadditions
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