Rhodium(I)-Catalyzed [4+1] Cycloaddition Reactions of α,β-Unsaturated Imines with Terminal Alkynes for the Preparation of Pyrrole Derivatives

2009 ◽  
Vol 48 (44) ◽  
pp. 8318-8320 ◽  
Author(s):  
Akio Mizuno ◽  
Hiroyuki Kusama ◽  
Nobuharu Iwasawa
Keyword(s):  
Cycloaddition Reactions ◽  
Terminal Alkynes ◽  
Pyrrole Derivatives

Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

2019 ◽  
Vol 84 (14) ◽  
pp. 8948-8958 ◽  
Author(s):  
Shaista Sultan ◽  
Muneer-ul-Shafi Bhat ◽  
Masood Ahmad Rizvi ◽  
Bhahwal Ali Shah
Keyword(s):  
Visible Light ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes

New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click” Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine

2018 ◽  
Vol 15 (4) ◽  
pp. 552-565 ◽  
Author(s):  
Nitin Kore ◽  
Pavel Pazdera
Keyword(s):  
Click Chemistry ◽  
Nucleophilic Substitution ◽  
Cyano Group ◽  
Catalytic Action ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes ◽  
Terminal Alkyne ◽  
Aryl Azide ◽  
Catalytic Application ◽  
Novel Synthesis

Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic, and heterocyclic terminal alkynes and corresponding 1,4-disubstituted 1,2,3-triazoles were obtained almost in the quantitative yields. The cycloaddition reactions of aryl azide with nitriles consisting α-hydrogen on carbon attached to cyano group under catalytic action of the title supported Cu(I) ended up with the formation of 1,4- disubstituted 1,2,3-triazol-5-amines in quantitative yields. The title catalyst found to be active for nucleophilic substitution of aide group (-N3) to 4-Iodoanisole. Conclusion: It was found that both studied Azide-Alkyne cycloaddition and Azide-Nitrile cycloaddition syntheses are regioselective and quantitative in yield. The title catalyst used is economical, easily preparable, separable, and recyclable. Therefore, the studied syntheses may be regarded as environmentally clean and green processes.

3 Ruthenium-Catalyzed Azide–Alkyne Cycloaddition (RuAAC)

2022 ◽  
Author(s):  
A. J. Paterson ◽  
T. Beke-Somfai ◽  
N. Kann
Keyword(s):  
High Selectivity ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes ◽  
Organic Azides ◽  
Internal Alkynes ◽  
Ruthenium Catalysis

AbstractUnder ruthenium catalysis, 1,5-disubstituted 1,2,3-triazoles can be accessed with high selectivity from terminal alkynes and organic azides via a ruthenium-catalyzed azide–alkyne cycloaddition (RuAAC) reaction. These conditions also allow the use of internal alkynes, providing access to 1,4,5-trisubstituted 1,2,3-triazoles. This chapter reviews the scope and limitations of the RuAAC reaction, as well as selected applications. A brief mention of azide–alkyne cycloaddition reactions catalyzed by other metals is also included.

Thermal [4p+2p]-Type Cycloaddition Reactions of Pyrrole Derivatives with 3-Cyanocyclopropene Generated in situ

Heterocycles ◽  
1989 ◽  
Vol 29 (11) ◽  
pp. 2135 ◽  
Author(s):  
Katsuhiro Saito ◽  
Kazuaki Ito ◽  
Kensuke Takahashi
Keyword(s):  
Cycloaddition Reactions ◽  
Pyrrole Derivatives
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