A Catalyst-Free Self-Catalyzed [3+2] Cycloaddition Reaction of 3-Isothiocyanato Oxindoles and Vinylpyridines

2018 ◽  
Vol 2018 (35) ◽  
pp. 4905-4916 ◽  
Author(s):  
Hou-Ze Gui ◽  
Yin Wei ◽  
Min Shi
Keyword(s):  
Cycloaddition Reaction ◽  
Catalyst Free

scholarly journals Tricarbonyl triazolato Re(i) compounds of pyridylbenzimidazole ligands: spectroscopic and antimicrobial activity evaluation

RSC Advances ◽  
2021 ◽  
Vol 11 (37) ◽  
pp. 22715-22722
Author(s):  
Ahmed M. Mansour
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Catalyst Free ◽  
Activity Evaluation

The antimicrobial activity and solvatochromism properties of mono- and binuclear tricarbonyl triazolato Re(i) complexes of pyridylbenzimidazole, formed by catalyst-free [3+2] cycloaddition reaction, were examined.

A Catalyst-Free Cycloaddition Reaction: Access to Spiro[chroman-3,2’-indene-1’,3’-dione] Scaffolds

2017 ◽  
Vol 2 (35) ◽  
pp. 11380-11383 ◽  
Author(s):  
Yuzhe Han ◽  
Yingzu Zhu ◽  
Pangmiaomiao Zhang ◽  
Wenjun Li ◽  
Pengfei Li
Keyword(s):  
Cycloaddition Reaction ◽  
Catalyst Free

Beyond the Alternatives that Switch the Mechanism of the 1,3-Dipolar CyCloadditions from Concerted to Stepwise or Vice Versa: A Literature Review

2016 ◽  
Vol 41 (4) ◽  
pp. 331-344 ◽  
Author(s):  
Seyyed Amir Siadati
Keyword(s):  
Organic Chemistry ◽  
Literature Review ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Stepwise Mechanism ◽  
Dipolar Cycloadditions ◽  
Catalyst Free ◽  
Number Of Factors ◽  
Reaction Channels ◽  
The 1960S

For several decades, the concerted or stepwise character of the mechanism of the 1,3-dipolar cycloaddition reaction has been one of the most debated issues in the field of organic chemistry. The significance of this problem is due to the fact that in a catalyst-free 1,3-dipolar cycloaddition, when the mechanism switches from concerted to stepwise, the stereospecificity is lost and thus unwanted stereoisomers may emerge. The first proposals about the mechanism of the 1,3-dipolar reaction were due to Huisgen (concerted model) and subsequently by Firestone (two-step diradical channel) in the 1960s. After a decade of debate, most researchers accepted the concerted model for the reaction, but during these years, researchers reported some examples of the stepwise mechanism for catalyst-free 1,3-dipolar cycloadditions. This review attempts to find a number of factors that could influence the reaction channels and switch the mechanism from concerted to stepwise, or vice versa.

Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles

2016 ◽  
Vol 8 (41) ◽  
pp. 28136-28142 ◽  
Author(s):  
Na Kong ◽  
Sheng Xie ◽  
Juan Zhou ◽  
Margarita Menéndez ◽  
Dolores Solís ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Catalyst Free

Catalyst-Free Process for the Synthesis of 5-Aryl-2-Oxazolidinones via Cycloaddition Reaction of Aziridines and Carbon Dioxide

Synlett ◽  
2010 ◽  
Vol 2010 (14) ◽  
pp. 2159-2163 ◽  
Author(s):  
Liang-Nian He ◽  
Xiao-Yong Dou ◽  
Zhen-Zhen Yang ◽  
Jing-Lun Wang
Keyword(s):  
Carbon Dioxide ◽  
Cycloaddition Reaction ◽  
Catalyst Free ◽  
Free Process

scholarly journals Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides

2016 ◽  
Vol 12 ◽  
pp. 2390-2401 ◽  
Author(s):  
Ilya V Efimov ◽  
Marsel Z Shafikov ◽  
Nikolai A Beliaev ◽  
Natalia N Volkova ◽  
Tetyana V Beryozkina ◽  
...  
Keyword(s):  
Room Temperature ◽  
Cycloaddition Reaction ◽  
Theoretical Studies ◽  
Dispersion Correction ◽  
Dioxane Solution ◽  
Theoretical Methods ◽  
Effective Catalyst ◽  
Nitrile Oxides ◽  
Catalyst Free ◽  
Experimental And Theoretical Studies

Reactions of β-azolyl enamines and nitrile oxides were studied by both experimental and theoretical methods. (E)-β-(4-Nitroimidazol-5-yl), (5-nitroimidazol-4-yl) and isoxazol-5-yl enamines smoothly react regioselectively at room temperature in dioxane solution with aryl, pyridyl, and cyclohexylhydroxamoyl chlorides without a catalyst or a base to form 4-azolylisoxazoles as the only products in good yields. The intermediate 4,5-dihydroisoxazolines were isolated as trans isomers during the reaction of (E)-β-imidazol-4-yl enamines with aryl and cyclohexylhydroxamoyl chlorides. Stepwise and concerted pathways for the reaction of β-azolyl enamines with hydroxamoyl chlorides were considered and studied at the B3LYP/Def2-TZVP level of theory combined with D3BJ dispersion correction. The reactions of benzonitrile oxide with both E- and Z-imidazolyl enamines have been shown to proceed stereoselectively to form trans- and cis-isoxazolines, respectively. The preference of E-isomers over Z-isomers, driven by the higher stability of the former, apparently controls the stereoselectivity of the investigated cycloaddition reaction with benzonitrilе oxide. Based on the reactivity of azolyl enamines towards hydroxamoyl chlorides, a novel, effective catalyst-free method was elaborated to prepare 4-azolyl-5-substituted isoxazoles that are otherwise difficult to obtain.

scholarly journals Catalyst-free room-temperature iClick reaction of molybdenum(ii) and tungsten(ii) azide complexes with electron-poor alkynes: structural preferences and kinetic studies

2017 ◽  
Vol 46 (39) ◽  
pp. 13386-13396 ◽  
Author(s):  
Paul Schmid ◽  
Matthias Maier ◽  
Hendrik Pfeiffer ◽  
Anja Belz ◽  
Lucas Henry ◽  
...  
Keyword(s):  
Room Temperature ◽  
Cycloaddition Reaction ◽  
Kinetic Studies ◽  
Catalyst Free ◽  
Structural Preferences ◽  
And Tungsten

The azide complexes [M(η3-allyl)(N3)(bpy)(CO)2] with M = Mo, W smoothly react in a [3 + 2] cycloaddition reaction with electron-poor alkynes.

Catalyst free boron carbon bond cleavage and facile formation of five-membered PNBCC heterocycles

2017 ◽  
Vol 46 (44) ◽  
pp. 15190-15194 ◽  
Author(s):  
Rajarshi Dasgupta ◽  
Atanu Panda ◽  
Shiv Pal ◽  
Puthan Veetil Muhasina ◽  
Susmita De ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Cycloaddition Reaction ◽  
Carbon Bond ◽  
Catalyst Free ◽  
Phosphorus Containing ◽  
Activated Alkynes ◽  
Boron Carbon

The [3 + 2] cycloaddition reaction of N(2,6-iPr2C6H3)(PPh2)(BCy2) (1) with activated alkynes led to the boron, phosphorus containing five-membered heterocycles (2–4) with facile cleavage of B–C bond and concomitant formation of a P–C bond with an ylidic character.

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