Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions

被引：70
|
作者：
Bai, Hui-Wen
Cai, Zhong-Jian
Wang, Shun-Yi [1 ]
Ji, Shun-Jun
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 12期
基金：
中国国家自然科学基金;
关键词：
RUTHENIUM-CATALYZED CYCLOADDITION; N-TOSYLHYDRAZONES; 1,3-DIPOLAR CYCLOADDITION; REGIOSPECIFIC SYNTHESIS; ALKYNE CYCLOADDITION; TERMINAL ALKYNES; ORGANIC AZIDES; NITROOLEFINS; AZOALKENES; PYRROLES;
D O I：
10.1021/acs.orglett.5b01000
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel synthetic approach toward 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles by aerobic oxidative cycloaddition of alpha-chlorotosylhydrazone with primary aryl amine has been developed. Significantly, the reaction proceeds smoothly to afford 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles under catalyst-free, metal-free, azide-free, and peroxide-free conditions.
引用
收藏
页码：2898 / 2901
页数：4
相关论文
共 50 条
  • [1] Photocatalytic generation of 1,4-disubstituted 1,2,3-triazoles under metal, oxidant and azide-free conditions
    Liu, Changhong
    Abdukerem, Dilshat
    Zhu, Wenli
    Xia, Kun
    Mao, Zechuan
    Abdukader, Ablimit
    GREEN SYNTHESIS AND CATALYSIS, 2024, 5 (01): : 62 - 67
  • [2] A Metal- and Azide-Free Multicomponent Assembly toward Regioselective Construction of 1,5-Disubstituted 1,2,3-Triazoles
    Wan, Jie-Ping
    Cao, Shuo
    Liu, Yunyun
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (18) : 9028 - 9033
  • [3] I2/TBPB Mediated Oxidative Reaction of N-Tosylhydrazones with Anilines: Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions
    Cai, Zhong-Jian
    Lu, Xin-Mou
    Zi, You
    Yang, Chao
    Shen, Ling-Jie
    Li, Jian
    Wang, Shun-Yi
    Ji, Shun-Jun
    ORGANIC LETTERS, 2014, 16 (19) : 5108 - 5111
  • [4] 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
  • [5] A two-step continuous flow synthesis of 1,4-disubstituted 1,2,3-triazoles under metal- and azide-free conditions
    Gu, Jiajia
    Fang, Zheng
    Yang, Zhao
    Li, Xin
    Zhu, Ning
    Wan, Li
    Wei, Ping
    Guo, Kai
    RSC ADVANCES, 2016, 6 (92): : 89073 - 89079
  • [6] Metal-free synthetic approaches to 1,5-disubstituted 1,2,3-triazoles
    Malkova, Ksenia
    Bubyrev, Andrey
    Balalaie, Saeed
    Dar'in, Dmitry
    Krasavin, Mikhail
    TETRAHEDRON LETTERS, 2022, 112
  • [7] Metal-free and azide-free synthesis of 1,2,3-triazoles derivatives
    Ahmed, Mukhtiar
    Razaq, Hamaela
    Faisal, Muhammad
    Siyal, Ali N.
    Haider, Azeem
    SYNTHETIC COMMUNICATIONS, 2017, 47 (13) : 1193 - 1200
  • [8] 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
  • [9] A novel route to 1,4-disubstituted-1,2,3-triazoles through metal-free decarboxylative azide-alkene cycloaddition
    Rengasamy, R.
    Vijayalakshmi, K.
    Punitha, N.
    Raj, J. Paul
    Karthikeyan, K.
    Elangovan, J.
    TETRAHEDRON LETTERS, 2021, 84
  • [10] Ruthenium-Free Preparation of 1,5-Disubstituted Triazoles by Alkylative Debenzylation of 1,4-Disubstituted Triazoles
    Page, Philip C. Bulman
    Stephenson, G. Richard
    Harvey, James
    Slawin, Alexandra M. Z.
    SYNLETT, 2016, 27 (17) : 2500 - 2504
12345