A NHC-catalyzed 1,3-dipolar cycloaddition reaction of allyl ketones with azides: direct access to 1,4,5-trisubstituted 1,2,3-triazoles

2017 ◽  
Vol 15 (20) ◽  
pp. 4286-4290 ◽  
Author(s):  
Huijun Yuan ◽  
Lili Zhang ◽  
Zhantao Liu ◽  
Yang Liu ◽  
Jian Wang ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
High Yields

A NHC-catalyzed 1,3-dipolar cycloaddition reaction of allyl ketones with azides has been developed. This strategy could generate 1,4,5-trisubstituted 1,2,3-triazoles in high yields and regioselectivities in the presence of a 20 mol% N-heterocyclic carbene catalyst. A broad substrate scope of this process is also presented.

Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: direct access to 3,4,5-trisubstituted isoxazoles

2016 ◽  
Vol 14 (23) ◽  
pp. 5246-5250 ◽  
Author(s):  
Xiao Zhou ◽  
Xianhong Xu ◽  
Zhenyan Shi ◽  
Kun Liu ◽  
Hua Gao ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
High Yields

Enolate-mediated [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of β-functionalized ketones with nitrile oxides have been developed. This strategy could generate 3,4,5-trisubstituted isoxazole in high yields and regioselectivities.

Direct access to 1,4-disubstituted 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of α,β-unsaturated esters with azides

RSC Advances ◽  
2015 ◽  
Vol 5 (108) ◽  
pp. 88816-88820 ◽  
Author(s):  
Wenjun Li ◽  
Xiao Zhou ◽  
Yepeng Luan ◽  
Jian Wang
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Unsaturated Esters ◽  
High Yields

DBU-catalyzed organocatalytic 1,3-dipolar cycloaddition reactions of α,β-unsaturated esters with azides have been developed. This strategy generates 1,4-disubstituted 1,2,3-triazoles in high yields with high regioselectivities.

Direct access to 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of allyl ketones with azides

2014 ◽  
Vol 16 (6) ◽  
pp. 3003-3006 ◽  
Author(s):  
Wenjun Li ◽  
Zhiyun Du ◽  
Jiayao Huang ◽  
Qianfa Jia ◽  
Kun Zhang ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition

A general organocatalytic 1,3-dipolar cycloaddition reaction between allyl ketones and various azides is reported. The reaction is catalyzed by a secondary amine to generate substituted 1,2,3-triazoles with high levels of regioselectivity.

Stepwise π-extension of meso-alkylidenyl porphyrins through sequential 1,3-dipolar cycloaddition and redox reactions

2014 ◽  
Vol 50 (66) ◽  
pp. 9277-9280 ◽  
Author(s):  
Dowoo Park ◽  
Seung Doo Jeong ◽  
Masatoshi Ishida ◽  
Chang-Hee Lee
Keyword(s):  
Redox Reactions ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
High Yields

Novel pi-extended,meso-malonylidene porphyrins have been synthesized in high yields by 1,3-dipolar cycloaddition reaction with the azomethine ylide.

Simple, stepwise and alternative syntheses of indolyl triazoles via Huisgen,s 1, 3-dipolar cycloaddition reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Ch. Venkata Ramana Reddy ◽  
G. Ganga Reddy
Keyword(s):  
Reaction Time ◽  
Addition Reaction ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Spectroscopic Methods ◽  
Aryl Azides ◽  
Simple Processing ◽  
High Yields

: A series of new 2-((1-((1-(4-methoxy-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)1H-indol-3-yl)me thylene)malononitrile derivatives were synthesized by the 1,3 dipolar cyclo addition reaction (click reaction) of 2-((1-(prop-2-yn-1-yl)-1H-indol-3-yl)methylene)malononitrile with different aryl azides in the presence of sodium ascorbate and copper sulphate in good yields. The advantages of this method are efficient, clean, high yields, easy workup procedures and shorter reaction time. These reactions are very facile giving products by simple processing that does not require purification by column chromatography. All the newly synthesized compounds were confirmed by spectroscopic methods.

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 267-271 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Atiyeh Moafi ◽  
Behzad Jafari ◽  
Alexander Vilinger ◽  
Peter Langer
Keyword(s):  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
Relative Stereochemistry ◽  
High Yields

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

Direct access to stabilized CuI using cuttlebone as a natural-reducing support for efficient CuAAC click reactions in water

RSC Advances ◽  
2016 ◽  
Vol 6 (68) ◽  
pp. 63613-63623 ◽  
Author(s):  
Sara S. E. Ghodsinia ◽  
Batool Akhlaghinia ◽  
Roya Jahanshahi
Keyword(s):  
Heterogeneous Catalyst ◽  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Click Reactions ◽  
Highly Active ◽  
The One ◽  
Reaction In Water

Cuttlebone@CuCl2 as a highly active, versatile, and green heterogeneous catalyst was investigated for the efficient preparation of 1,4-disubstituted 1,2,3-triazoles through the one-pot Huisgen 1,3-dipolar cycloaddition reaction in water.

Organocatalytic 1,3-dipolar [3+3] cycloaddition reaction of 1,2-cyclohexanedione with azides: direct access to highly substituted 1,2,3-triazoles

2016 ◽  
Vol 40 (8) ◽  
pp. 6559-6563 ◽  
Author(s):  
Xianhong Xu ◽  
Zhenyan Shi ◽  
Wenjun Li
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Cycloaddition Reactions ◽  
High Yields

Enamine-mediated 1,3-dipolar [3+3] cycloaddition reactions of 1,2-cyclohexanedione with azides have been developed. This strategy could generate highly substituted 1,2,3-triazoles in high yields and high levels of regioselectivities. It is demonstrated that various types of products could be obtained with different organocatalysts and substrates.

Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid

Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1541-1545 ◽  
Author(s):  
Yuan Jin ◽  
Yasuhiro Honma ◽  
Hisashi Morita ◽  
Masamichi Miyagawa ◽  
Takahiko Akiyama
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Vinyl Ether ◽  
31P Nmr ◽  
Cycloaddition Reaction ◽  
Enantioselective Synthesis ◽  
Dipolar Cycloaddition ◽  
New Approach ◽  
Chiral Phosphoric Acid ◽  
High Yields

A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1H and 31P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.

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