Regiospecific Synthesis of N2-Aryl 1,2,3-Triazoles from 2,5-Disubstituted Tetrazoles via Photochemically Generated Nitrile Imine Intermediates

被引：10

作者：

Stewart, Sam ^{[1
]}

Harris, Robert ^{[1
]}

Jamieson, Craig ^{[2
]}

机构：

[1] GlaxoSmithKline Med Res Ctr, Stevenage SG1 2NY, Herts, England

[2] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland

来源：

SYNLETT | 2014年 / 25卷 / 17期

关键词：

photochemistry; regioselectivity; tetrazole; triazole; indazole; EFFICIENT SYNTHESIS; TRIAZOLE; CYCLOADDITIONS; FLUOROPHORES;

D O I：

10.1055/s-0034-1379010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of N2-aryl 1,2,3-triazoles from 2,5-disubstituted tetrazoles was achieved under photochemical conditions. This simple and mild one-step reaction provides regiospecific access to 2,4,5-substituted 1,2,3-triazoles via a nitrile imine intermediate. Syntheses of alkyl and heterocylic derivatives were also investigated.

引用

页码：2480 / 2484

页数：5

共 50 条

[1] An Organocatalytic Regiospecific Synthesis of 1,5-Disubstituted 4-Thio-1,2,3-triazoles and 1,5-Disubstituted 1,2,3-Triazoles
Ramachary, Dhevalapally B.
Krishna, Patoju M.
Gujral, Jagjeet
Reddy, G. Surendra
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) : 16775 - 16780
[2] Base-Promoted Regiospecific Synthesis of Fully Substituted 1,2,3-Triazoles and 1,5-Disubstituted 1,2,3-Triazoles
Zhang, Xueying
Cui, Xue
Wang, Wei
Zeng, Tingting
Wang, Yan
Tan, Yinfeng
Liu, Dongyan
Wang, Xuesong
Li, Youbin
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (12) : 2176 - 2183
[3] A New Method for the Synthesis of 1,5-Disubstituted 1,2,3-Triazoles via Triazolium Salt Intermediates
Koguchi, Shinichi
Izawa, Kazuki
SYNTHESIS-STUTTGART, 2012, 44 (23): : 3603 - 3608
[4] Synthesis of 2-tetrafluoropyridyl-4,5-disubstituted 1,2,3-triazoles
Beyki, Khalil
Maghsoodlou, Malek Taher
Heydari, Reza
SPRINGERPLUS, 2016, 5
[5] Facile synthesis of 1,5-disubstituted 1,2,3-triazoles by the regiospecific alkylation of a ruthenium triazolato complex
Chang, Chao-Wan
Lee, Gene-Hsiang
DALTON TRANSACTIONS, 2019, 48 (06) : 2028 - 2037
[6] Regioselective Synthesis of N2-Aryl 1,2,3-Triazoles via Electro- oxidative Coupling of Enamines and Aryldiazonium Salts
Baidya, Mrinmay
Mallick, Samrat
De Sarkar, Suman
ORGANIC LETTERS, 2022, 24 (06) : 1274 - 1279
[7] A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
Cheng, Guolin
Zeng, Xiaobao
Shen, Jinhai
Wang, Xuesong
Cui, Xiuling
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13265 - 13268
[8] Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
Bubyrev, Andrey
Malkova, Ksenia
Kantin, Grigory
Dar'in, Dmitry
Krasavin, Mikhail
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17516 - 17522
[9] Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
N. T. Pokhodylo
M. A. Tupychak
M. D. Obushak
Russian Journal of Organic Chemistry, 2022, 58 : 209 - 218
[10] Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
Pokhodylo, N. T.
Tupychak, M. A.
Obushak, M. D.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (02) : 209 - 218

← 1 2 3 4 5 →