Base-Mediated Tandem [3+2] Cycloaddition/Ring Openning Reaction of Arylhydrazonoyl Chlorides with Arylnitroso Compounds for Synthesis of Substituted Diazene Oxides

被引:3
|
作者
Li, Yi [1 ]
Xu, Weinan [1 ]
Lei, Xidan [1 ]
Xi, Jiangbo [1 ]
Zou, Jing [1 ]
Wang, Gang [1 ]
He, Zhao-Lin [1 ]
机构
[1] Wuhan Inst Technol, Engn Res Ctr Phosphorus Resources Dev & Utilizat, Sch Chem & Environm Engn, Key Lab Green Chem Engn Proc,Minist Educ,Hubei Ke, Wuhan 430205, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 19期
基金
中国国家自然科学基金;
关键词
NITRILE IMINES; 1,3-DIPOLAR CYCLOADDITION; NITROSOBENZENES; BIOSYNTHESIS; NITRILIMINES; PERFORMANCE; DERIVATIVES; AZO;
D O I
10.1021/acs.joc.3c01427
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A base-mediated tandem [3 + 2] cycloaddition/ring opening reaction of nitrilimines generated from arylhydrazonoyl chlorides with arylnitroso compounds has been developed. This protocol provides a novel and rapid approach for the synthesis of substituted azoxy compounds under mild conditions with moderate to good yields and a broad substrate scope.
引用
收藏
页码:14200 / 14204
页数:5
相关论文
共 50 条
  • [21] Base-catalysed oxidative [3+2]cycloaddition reaction of [60]fullerene with beta-dicarbonyl compounds
    Ohno, M
    Yashiro, A
    Eguchi, S
    CHEMICAL COMMUNICATIONS, 1996, (03) : 291 - 292
  • [22] Silver-Mediated [3+2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles
    Yang, Hefei
    Lu, Shu-Ning
    Chen, Zhengkai
    Wu, Xiao-Feng
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (05): : 4361 - 4370
  • [23] Synthesis of 5-trifluoromethyl-1,2,3-triazoles via base-mediated cascade annulation of diazo compounds with trifluoroacetimidoyl chlorides
    Yang, Hefei
    Xu, Tian-Hui
    Lu, Shu-Ning
    Chen, Zhengkai
    Wu, Xiao-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13) : 3440 - 3445
  • [24] Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition
    Arena, Giada
    Chen, C. Chun
    Leonori, Daniele
    Aggarwal, Varinder K.
    ORGANIC LETTERS, 2013, 15 (16) : 4250 - 4253
  • [25] One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition
    Pirali, Tracey
    Tron, Gian Cesare
    Zhu, Jieping
    ORGANIC LETTERS, 2006, 8 (18) : 4145 - 4148
  • [26] Synthesis of substituted cyclopentanes via intramolecular [3+2] cycloaddition of silylnitronates generated by nitro-Michael reaction
    Lozanova, A. V.
    Shashkov, A. S.
    Veselovsky, V. V.
    RUSSIAN CHEMICAL BULLETIN, 2015, 64 (02) : 379 - 384
  • [27] Synthesis of substituted cyclopentanes via intramolecular [3+2] cycloaddition of silylnitronates generated by nitro-Michael reaction
    A. V. Lozanova
    A. S. Shashkov
    V. V. Veselovsky
    Russian Chemical Bulletin, 2015, 64 : 379 - 384
  • [28] Lewis acid- and/or Lewis base-catalyzed [3+2] cycloaddition reaction: synthesis of pyrazoles and pyrazolines
    Krishna, Palakodety Radha
    Sekhar, Empati Raja
    Mongin, Florence
    TETRAHEDRON LETTERS, 2008, 49 (48) : 6768 - 6772
  • [29] Synthesis of 2-aminobenzofurans via base-mediated [3+2] annulation of N-phenoxy amides with gem-difluoroalkenes
    Chen, Kaifeng
    Chen, Weijie
    Chen, Fangyuan
    Zhang, Haiman
    Xu, Huiying
    Zhou, Zhi
    Yi, Wei
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (16) : 4452 - 4458
  • [30] Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: efficient synthesis of 1,4,5-trisubstituted imidazoles
    Cai, Jinxiong
    Bai, Haijie
    Wang, Yuan
    Xu, Xianxiu
    Xie, Haiming
    Liu, Jun
    CHEMICAL COMMUNICATIONS, 2019, 55 (26) : 3821 - 3824