Highly Efficient Cycloaddition Reaction of 1,3-Diynes with Sodium Azide: A New Way to 5-Substituted-4-acetylene-1H-1,2,3-triazoles

被引：9

作者：

Tang, Jia-Liang ^{[1
]}

Ming, Ling ^{[1
]}

Zhao, Xiao-Ming ^{[1
]}

机构：

[1] Tongji Univ, Dept Chem, State Key Lab Pollut Control & Resource Reuse, Shanghai 200092, Peoples R China

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2016年 / 53卷 / 05期

关键词：

TERMINAL ALKYNES; 1,3-DIPOLAR CYCLOADDITIONS; CLICK CHEMISTRY; HYDROAMINATION; HYDRATION; ALLENES; CUCL;

D O I：

10.1002/jhet.1950

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cycloaddition reaction of a range of 1,3-diynes with sodium azide has been realized, which provided 5-substituted-4-acetylene-1H-1,2,3-triazoles in 75-99% yields. The chemical structures of the new compounds 3 are established by IR, NMR, Mass, and HRMS.

引用

页码：1367 / 1370

页数：4

共 50 条

[31] First synthesis of both 1-aryl-4-[(E)-alk-1-enyl]-1H-1,2,3-triazoles and 1-aryl-4-[(Z)-1-(trimethylsilyl)alk-1-enyl]-1H-1,2,3-triazoles: assembly of π-extended 1,2,3-triazoles using a cross-coupling/click reaction sequence
Oikawa, Asuka
Kindaichi, Gan
Shimotori, Yasutaka
Hoshi, Masayuki
TETRAHEDRON, 2016, 72 (29) : 4205 - 4213
[32] Multi-component reaction for the preparation of 1,5-disubstituted 1,2,3-triazoles by in-situ generation of azides and nickel-catalyzed azide-alkyne cycloaddition
Camberlein, Virgyl
Kraupner, Nicolas
Karroum, Nour Bou
Lipka, Emmanuelle
Deprez-Poulain, Rebecca
Deprez, Benoit
Bosc, Damien
TETRAHEDRON LETTERS, 2021, 73
[33] Visible-light-promoted three-component cycloaddition reaction: synthesis of 4-functionalized 1,5-disubstituted 1,2,3-triazoles
Kumar, Atul
Kumar, Navaneet
Bhadoria, Deepak
GREEN CHEMISTRY, 2021, 23 (20) : 7987 - 7995
[34] [Bmim]OH mediated Cu-catalyzed azide-alkyne cycloaddition reaction: A potential green route to 1,4-disubstituted 1,2,3-triazoles
Ali, Abdul Aziz
Konwar, Manashjyoti
Chetia, Mitali
Sarma, Diganta
TETRAHEDRON LETTERS, 2016, 57 (50) : 5661 - 5665
[35] A highly efficient copper(I) catalyst for the 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes in water: regioselective synthesis of 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles
Garcia-Alvarez, Joaquin
Diez, Josefina
Gimeno, Jose
GREEN CHEMISTRY, 2010, 12 (12) : 2127 - 2130
[36] Synthesis of Novel 1,4-Substituted 1,2,3-Triazoles by Water-Soluble (Salicyladimine)2Cu Complex Catalyzed Azide-Alkyne Cycloaddition in Water
Liu, Yang
Liu, Ping
Liu, Yan
Wei, Yu
LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (08) : 557 - 565
[37] 'Green' synthesis of 1,4-disubstituted 5-iodo-1,2,3-triazoles under neat conditions, and an efficient approach of construction of 1,4,5-trisubstituted 1,2,3-triazoles in one pot
Wang, Dong
Chen, Si
Chen, Baohua
TETRAHEDRON LETTERS, 2014, 55 (51) : 7026 - 7028
[38] Design and Synthesis of New 5-aryl-4-Arylethynyl-1H-1,2,3-triazoles with Valuable Photophysical and Biological Properties
Efremova, Mariia M.
Govdi, Anastasia I.
Frolova, Valeria V.
Rumyantsev, Andrey M.
Balova, Irina A.
MOLECULES, 2021, 26 (09):
[39] Efficient Atropodiastereoselective Access to 5,5'- Bis-1,2,3triazoles: Studies on 1-Glucosylated 5-Halogeno 1,2,3-Triazoles and Their 5-Substituted Derivatives as Glycogen Phosphorylase Inhibitors
Goyard, David
Chajistamatiou, Aikaterini S.
Sotiropoulou, Anastasia I.
Chrysina, Evangelia D.
Praly, Jean-Pierre
Vidal, Sebastien
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (18) : 5423 - 5432
[40] Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles to Design New Acetylcholinesterase Inhibitors: Fast and Easy Generation of 4-Methylcoumarins/1,2,3-triazoles Conjugates via Click Chemistry
Torres, Fernando C.
Goncalves, Guilherme A.
Vanzolini, Kenia L.
Merlo, Aloir A.
Gauer, Bruna
Holzschuh, Maribete
Andrade, Saulo
Piedade, Maristela
Garcia, Solange C.
Carvalho, Ivone
von Poser, Gilsane L.
Kawano, Daniel F.
Eifler-Lima, Vera L.
Cass, Quezia B.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2016, 27 (09) : 1541 - 1550

← 1 2 3 4 5 →