Study on the green click-chemistry synthesis of 4-trifluoroacetyl-1,2,3-triazoles

被引：8

作者：

Han, Jie ^{[1
]}

Ran, Jian-Xiong ^{[1
]}

Chen, Xiu-Ping ^{[1
]}

Wang, Zhong-Hua ^{[1
,2
]}

Wu, Fan-Hong ^{[1
]}

机构：

[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai, Peoples R China

[2] Shanghai Engn Res Ctr Pharmaceut Progress, Shanghai 201203, Peoples R China

来源：

TETRAHEDRON | 2018年 / 74卷 / 49期

基金：

中国国家自然科学基金;

关键词：

Click-chemistry; Metal-free; Solvent free; Anti-cancer activities; 1,3-DIPOLAR CYCLOADDITION; REACTION METRICS; AZIDE; ROUTE; REGIOSELECTIVITY; 1,2,3-TRIAZOLES; DERIVATIVES; ANTICANCER; IMPACT;

D O I：

10.1016/j.tet.2018.10.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free and solvent free click-chemistry procedure has been revealed for the synthesis of 4-trifluoroacetyl-1,2,3-triazoles from corresponding azides and alkyne with high yield and selectivity. The pure products could be easily obtained via crystallization of the reaction mixture (standing for 1 day). Among the 4-trifluoroacetyl-1,2,3-triazoles, 3ba showed the best anticancer activity against HepG2 cell with IC50 of 0.0267 mu mol/ml. This method has the advantages of less pollution, low cost, simple treatment and more efficiency. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：6985 / 6992

页数：8

共 50 条

[31] The fate of heterogeneous catalysis & click chemistry for 1,2,3-triazoles: Nobel prize in chemistry 2022
Kumar, Vijay
Lal, Kashmiri
Naveen, Ram Kumar
Tittal, Ram Kumar
CATALYSIS COMMUNICATIONS, 2023, 176
[32] Innovation for Cu-catalyzed azide/alkyne click chemistry: Synthesis of 4,5′-bis-1,2,3-triazoles
Ellison, Aubrey
Brisbois, Ronald
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[33] A NEW SYNTHESIS OF 4-AROYL-1,2,3-TRIAZOLES
NESMEYAN.AN
RYBINSKA.MI
DOKLADY AKADEMII NAUK SSSR, 1966, 167 (01): : 109 - &
[34] SYNTHESIS OF METHYLATED 4-BROMODINITROMETHYL-1,2,3-TRIAZOLES
LADYZHNIKOVA, TD
MANUEL, DV
ALTUKHOV, KV
ZHURNAL ORGANICHESKOI KHIMII, 1991, 27 (10): : 2243 - 2244
[35] Tandem click preparation of 4-formyl- and 4-imido-1,2,3-triazoles
Fletcher, James T.
Christensen, Joseph A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[36] Synthesis, characterization, and antifungal activity of biaryl-based bis(1,2,3-triazoles) using click chemistry
Manoj Gaur
Mayurika Goel
L. Sridhar
Tara Devi S. Ashok
S. Prabhakar
P. Dureja
P. Raghunathan
S. V. Eswaran
Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 283 - 288
[37] Microwave-Assisted Click Chemistry Synthesis of 1,2,3-Triazoles from Aryldiazonium Silica Sulfates in Water
Zarei, Amin
Khazdooz, Leila
Hajipour, Abdol R.
Aghaei, Hamidreza
Azizi, Ghobad
SYNTHESIS-STUTTGART, 2012, 44 (21): : 3353 - 3360
[38] 1,2,3-TRIAZOLES .2. 4-AMINO-5-AMINOMETHYL-1,2,3-TRIAZOLES
ALBERT, A
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (15): : 1634 - 1639
[39] Click chemistry based multicomponent approach in the synthesis of spirochromenocarbazole tethered 1,2,3-triazoles as potential anticancer agents
Chavan, Pramod, V
Desai, Uday, V
Wadgaonkar, Prakash P.
Tapase, Savita R.
Kodam, Kisan M.
Choudhari, Amit
Sarkar, Dhiman
BIOORGANIC CHEMISTRY, 2019, 85 : 475 - 486
[40] Synthesis, characterization, and antifungal activity of biaryl-based bis(1,2,3-triazoles) using click chemistry
Gaur, Manoj
Goel, Mayurika
Sridhar, L.
Ashok, Tara Devi S.
Prabhakar, S.
Dureja, P.
Raghunathan, P.
Eswaran, S. V.
MONATSHEFTE FUR CHEMIE, 2012, 143 (02): : 283 - 288

← 1 2 3 4 5 →