Nickel-Catalyzed Regio- and Enantioselective Annulation Reactions of 1,2,3,4-Benzothiatriazine-1,1(2H)-dioxides with Allenes

被引：97
|
作者：
Miura, Tomoya [1 ]
Yamauchi, Motoshi [1 ]
Kosaka, Akira [1 ]
Murakami, Masahiro [1 ]
机构：
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 29期
关键词：
annulation; asymmetric synthesis; nickel; nitrogen heterocycles; synthetic methods; DECARBONYLATIVE ADDITION; ASYMMETRIC CATALYSIS; ALKYNES; HETEROCYCLES; ANHYDRIDES; 1,2,3-BENZOTRIAZIN-4(3H)-ONES; TRANSANNULATION; CARBOAMINATION; INHIBITORS; INSERTION;
D O I：
10.1002/anie.201001918
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Figure Presented) Extrusion of N2:1,2,3,4-Benzothiatriazine1,1 (2H)-dioxides reacted with alienes in the presence of a nickel (0)/(R)-quinap complex to produce a variety of substituted 3,4-dihydro-1,2-benzothiazine1,1 (2H)-dioxides in a regio- and enantioselective fashion. An intermediate nickelacycle was generated through denitrogenative activation of the triazo moiety which allowed the intermolecular incorporation of an aliene group. quinap = 1-(2diphenylphosphino-1-naphthyl)isoquinoline. © 2010 Wiley-VCH Verlag GmbH & Co. KCaA, Weinheirn.
引用
收藏
页码：4955 / 4957
页数：3
相关论文
共 50 条
  • [1] Nickel-Catalyzed Denitrogenative Cyclization of 1,2,3,4-Benzothiatriazin-1,1(2H)-dioxides with Arynes To Synthesize Biary lSultams
    Thorat, Vijaykumar H.
    Tsai, Yu-Lin
    Huang, Yong-Ran
    Cheng, Chien-Hong
    Hsieh, Jen-Chieh
    ORGANIC LETTERS, 2022, 24 (15) : 2915 - 2920
  • [2] SOME 1,2,3,4-BENZOTHIATRIAZINE 1,1-DIOXIDES
    CHILDRESS, SJ
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1962, 51 (08) : 806 - &
  • [3] Enantioselective Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones by Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4(3H)-ones with Allenes
    Yamauchi, Motoshi
    Morimoto, Masao
    Miura, Tomoya
    Murakami, Masahiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (01) : 54 - +
  • [4] Enantioselective Nickel-Catalyzed Hydrosilylation of 1,1-Disubstituted Allenes
    Liu, Tao
    Mao, Xin-Rui
    Song, Shuo
    Chen, Zi-Yang
    Wu, Yichen
    Xu, Li-Ping
    Wang, Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (11)
  • [5] Nickel-Catalyzed Enantioselective Hydrosilylation of 1,1-Disubstituted Allenes
    Chen Shaowei
    Shen Xiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (03) : 1213 - 1214
  • [6] Radical-mediated chemo-divergent recyclization of 1,2,3,4-benzothiatriazine-1,1-dioxides: alkyl migration and dearomatization
    Nan, Jiang
    Yang, Shuai
    Huang, Guanjie
    Fan, Liangxin
    CHEMICAL COMMUNICATIONS, 2025, 61 (29) : 5503 - 5506
  • [7] Synthesis of biaryl sultams using visible-light-promoted denitrogenative cyclization of 1,2,3,4-benzothiatriazine-1,1-dioxides
    Han, Yue-Yue
    Wang, Hao
    Yu, Shouyun
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (08): : 953 - 956
  • [8] Nickel-Catalyzed Transannulation Reaction of 1,2,3,4-Benzothiatriazin-1,1(2H)-dioxide with Alkyne and the Detailed Investigation of Reaction Mechanism
    Thorat, Vijaykumar H.
    Chuang, Ya-Chu
    Hsieh, Chung-Hung
    Hsieh, Jen-Chieh
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [9] Nickel-Catalyzed Regio- and Enantioselective Hydroarylation of 1,3-Dienes with Indoles
    Cheng, Lei
    Li, Ming-Ming
    Li, Mao-Lin
    Xiao, Li-Jun
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CCS CHEMISTRY, 2022, 4 (08): : 2612 - 2619
  • [10] Catalytic Regio- and Enantioselective [4+2] Annulation Reactions of Non-activated Allenes by a Chiral Cationic Indium Complex
    Wang, Le
    Lv, Jian
    Zhang, Long
    Luo, Sanzhong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (36) : 10867 - 10871
12345