Synthesis of 2-alkyl triazoles with solvothermal conditions

被引：2

作者：

Ma, Youcai ^{[1
]}

Zhang, Xiaohui ^{[1
]}

Yang, Yawen ^{[1
]}

Hu, Liangzhen ^{[1
]}

Xiong, Yan ^{[1
,2
,3
,4
]}

机构：

[1] Chongqing Univ, Sch Chem & Chem Engn, Chongqing Key Lab Theoret & Computat Chem, Chongqing 401331, Peoples R China

[2] Nankai Univ, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China

[3] Xinjiang Inst Engn, Collaborat Innovat Ctr High Value Transformat Coal, Sch Chem & Environm Engn, Urumqi 830091, Xinjiang, Peoples R China

[4] Chongqing Univ, Sch Chem & Chem Engn, Chongqing Key Lab Theoret & Computat Chem, Chongqing 401331, Peoples R China

来源：

TETRAHEDRON | 2022年 / 113卷

关键词：

2-Alkyl triazoles; Metal-free; Nucleophilic substitution; Potassium carbonate; 3-Triazoles; N-ALKYLATION; BENZOTRIAZOLE; 1,2,3-TRIAZOLES; EFFICIENT; AMINATION; ANALOGS; AZIDES;

D O I：

10.1016/j.tet.2022.132765

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general protocol for the straightforward access to 2-alkyl triazoles with alkyl halides as the readily available alkylation reagents, by using a well-organized nucleophilic substitution strategy under metal free and solvothermal conditions has been developed. Various alkyl substitutions on 2-site of triazoles occurred and were mainly examined in the text. Particularly, the reactions between linear bisbromo alkanes and 1,2,3-triazoles were executed to yield bromoalkyl triazoles and bistriazoles, and realkylations of bromoalkyl triazoles were achieved through addition of triazoles. This procedure is convenient and generally affords the 2-alkylated products, which are slightly scarce under present synthetic methodologies. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：8

共 50 条

[31] THE ADRENAL HORMONES AND RELATED COMPOUNDS .3. SYNTHESIS OF 2-ALKYL ANALOGS
HOGG, JA
LINCOLN, FH
JACKSON, RW
SCHNEIDER, WP
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) : 6401 - 6402
[32] Convenient syntheses of 2-alkyl(aryl)-4,5-diphenyloxazoles and 2-alkyl(aryl)-4-phenyloxazoles
Pei, WW
Li, SH
Nie, XP
Li, YW
Pei, J
Chen, BZ
Wu, J
Ye, XL
SYNTHESIS-STUTTGART, 1998, (09): : 1298 - 1304
[33] Stereoselective synthesis of (E)-(2-alkyl)-(1-silylvinyl) selenides via hydrozirconation of alkyl silyl acetylenes
Xu, XH
Zheng, WX
Huang, X
SYNTHETIC COMMUNICATIONS, 1998, 28 (22) : 4165 - 4170
[34] Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts
Qu, Bo
Mangunuru, Hari P. R.
Wei, Xudong
Fandrick, Keith R.
Desrosiers, Jean-Nicolas
Sieber, Joshua D.
Kurouski, Dmitry
Haddad, Nizar
Samankumara, Lalith P.
Lee, Heewon
Savoie, Jolaine
Ma, Shengli
Grinberg, Nelu
Sarvestani, Max
Yee, Nathan K.
Song, Jinhua J.
Senanayake, Chris H.
ORGANIC LETTERS, 2016, 18 (19) : 4920 - 4923
[35] CONCERNING SYNTHESIS OF 2-ALKYL 2-DIMETHYLAMINO 1,3-DITHIOLANES - REPLY
FEUGEAS, C
OLSCHWAN.D
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1970, (05): : 2014 - &
[36] Synthesis and vesicle formation of ethyl 2-[2′-(F-alkyl)ethyl] 2-alkyl malonic acid disodium salts
Trabelsi, H
Szönyi, S
Reuter, P
Wehrli, E
Geribaldi, S
SUPRAMOLECULAR CHEMISTRY, 2001, 13 (05) : 583 - 591
[37] Synthesis of 2-alkyl and 2-aryl pyrimidines from β-chlorovinyl ketones of cyclopentanone type
Popov, SA
Tkachev, AV
SYNTHETIC COMMUNICATIONS, 2001, 31 (02) : 233 - 243
[38] Facile synthesis of 2-alkyl and 2-aryl-4-quinolones using microwave irradiation
Huang, ZZ
Wu, LL
Huang, X
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2000, 20 (01) : 88 - 90
[39] Stereoselective synthesis of (E)-2-alkyl and 2-phenyl-1-silylvinyl sulfides via hydrozirconation of alkyl silyl acetylenes
Zhong, P
Guo, MP
Huang, X
JOURNAL OF CHEMICAL RESEARCH-S, 2000, (06): : 298 - 299
[40] Double nucleophilic addition: A new synthesis of 2-alkyl and 2-phenyl-5-hydrazinopyridines.
Zhang, L
Tan, ZL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U164 - U164

← 1 2 3 4 5 →