Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles via 1,3‐Dipolar Cycloaddition/C–N Coupling of Propargyl Alcohols/amines and Aryl Azides

2018 ◽  
Vol 55 (12) ◽  
pp. 2683-2692
Author(s):  
Mohammad Bakherad ◽  
Ahmad Kakavand Ghalenoei ◽  
Ali Keivanloo
Keyword(s):  
Dipolar Cycloaddition ◽  
Aryl Azides ◽  
Propargyl Alcohols

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.

Synthesis of New Pyrazolenines and Cyclopropenyl Alcohols Directly from Propargyl Alcohols

2005 ◽  
Vol 2005 (5) ◽  
pp. 289-292 ◽  
Author(s):  
Naceur Hamdi ◽  
Pierre Henry Dixneuf ◽  
Youssef Arfaoui ◽  
Ezzeddine Haloui
Keyword(s):  
Double Bond ◽  
Good Yield ◽  
Dipolar Cycloaddition ◽  
Propargylic Alcohols ◽  
Propargyl Alcohols

The 1,3-dipolar cycloaddition of 2-diazopropane 1 to propargylic alcohols is regioselective and leads to 3H-pyrazoles 3 in good yield. The surprising formation of the tetrasubstitued pyrazolenine 4c from HC=CCH2OH and 1 can be explained via the 1,3-dipolar cycloadduct intermediate followed by a second cycloaddition of 1 to the C=C double bond and loss of dinitrogen. The photolysis of the antibacterial pyrazolenines 3 and 4 selectively gives α and β dimethylcyclopropenyl alcohols 5 and 6.

scholarly journals 1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles

2015 ◽  
Vol 137 (8) ◽  
pp. 2958-2966 ◽  
Author(s):  
Sheng Xie ◽  
Steven A. Lopez ◽  
Olof Ramström ◽  
Mingdi Yan ◽  
K. N. Houk
Keyword(s):  
Dipolar Cycloaddition ◽  
Aryl Azides

1,3-Dipolar Cycloaddition of Aza-Propargylglycine with Aryl Azides

Synfacts ◽  
2010 ◽  
Vol 2010 (11) ◽  
pp. 1311-1311 ◽  
Author(s):  
W. Lubell ◽  
C. Proulx
Keyword(s):  
Dipolar Cycloaddition ◽  
Aryl Azides

ChemInform Abstract: 1,3-Dipolar Cycloaddition of Aryl Azides to 1-Aryl-3-phenylprop-2-yn-1-ones.

ChemInform ◽  
1989 ◽  
Vol 20 (24) ◽  
Author(s):  
F. A. E. FOULI ◽  
M. E. SHABAN ◽  
E. I. EL-NAGDY ◽  
A. S. A. YOUSSEF
Keyword(s):  
Dipolar Cycloaddition ◽  
Aryl Azides

scholarly journals One-pot synthesis of 3-substituted-4H-[1,2,3] triazolo[5,1-c][1,4]oxazin-6(7H)-ones from propargyl alcohols, chloroacetyl chloride, and sodium azide

2020 ◽  
pp. 174751982094835
Author(s):  
Xiao-Lan Zhang ◽  
Mei-Hong Wei ◽  
Jun-Min Chen ◽  
Shou-Ri Sheng ◽  
Xiao-Ling Liu
Keyword(s):  
Sodium Azide ◽  
High Efficiency ◽  
Dipolar Cycloaddition ◽  
Chloroacetyl Chloride ◽  
One Pot ◽  
Product Yields ◽  
Simple Operation ◽  
One Pot Synthesis ◽  
Propargyl Alcohols

An efficient, one-pot synthesis of 3-substituted-4 H-[1,2,3]triazolo[5,1- c][1,4]oxazin-6(7 H)-ones is developed via sequential esterification, substitution, and 1,3-dipolar cycloaddition processes of various propargyl alcohols, chloroacetyl chloride, and sodium azide. This method provides a variety of novel 1,2,3-triazole-fused oxazinones and has several advantages including simple operation, high efficiency, and good-to-excellent product yields (80%–95%) without the need to isolate the ester and azide intermediates.

ChemInform Abstract: Azide-Enolate 1,3-Dipolar Cycloaddition as an Efficient Approach for the Synthesis of 1,5-Disubstituted 1,2,3-Triazoles from Alkyl/Aryl Azides and β-Ketophosphonates.

ChemInform ◽  
2016 ◽  
Vol 47 (25) ◽  
Author(s):  
Davir Gonzalez-Calderon ◽  
Aydee Fuentes-Benites ◽  
Eduardo Diaz-Torres ◽  
Carlos A. Gonzalez-Gonzalez ◽  
Carlos Gonzalez-Romero
Keyword(s):  
Dipolar Cycloaddition ◽  
Aryl Azides ◽  
Alkyl Aryl ◽  
Efficient Approach
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