Synthesis of Cyclopenta[b]indoles via Rhodium-Catalyzed Cascade Migration-Annulation of 1-Sulfonyl-1,2,3-triazoles and Indoles

被引：8
|
作者：
Xu, Huaping [1 ,2 ]
Wang, Heng [1 ]
Xu, Ze-Feng [1 ]
Duan, Shengguo [1 ]
Li, Chuan-Ying [1 ]
机构：
[1] Zhejiang Sci Tech Univ, Sch Chem & Chem Engn, Key Lab Surface & Interface Sci Polymer Mat Zhejia, Hangzhou 310018, Peoples R China
[2] Zhejiang Sci Tech Univ, Sch Mat Sci & Engn, Xiasha West Higher Educ Dist, Hangzhou 310018, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 10期
基金：
中国国家自然科学基金;
关键词：
migration-annulation; 1-sulfonyl-1,2,3triazoles; carbenes; cyclopenta[b]indoles; DEAROMATIVE 3+2 CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITIONS; 3-NITROINDOLES; FUNCTIONALIZATION; TRANSANNULATION; 1,2,3-TRIAZOLES; HETEROCYCLES; INDOLINES; CONSTRUCTION; ZWITTERION;
D O I：
10.1002/adsc.202300241
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A rhodium-catalyzed cascade 1,3-sulfinate migration, intermolecular [3 +2] annulation of 1-sulfonyl-1,2,3-triazoles and indoles was achieved. The one-pot protocol provided a method to construct cyclopenta[b]indoles bearing four stereocenters in 45% to 99% yields with 1.6:1 to > 20:1 diastereoselectivities. In addition, cyclopenta[b]indoles could be transformed into a variety of functionalized compounds, demonstrating the synthetic value of this migration-annulation strategy in ring system synthesis.
引用
收藏
页码：1623 / 1628
页数：6
相关论文
共 50 条
  • [1] Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles
    Duan, Shengguo
    An, Yuehui
    Xue, Bing
    Chen, Yidian
    Zhang, Wan
    Xu, Ze-Feng
    Li, Chuan-Ying
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (09) : 1831 - 1835
  • [2] Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3-triazoles with indoles: facile synthesis of functionalized tetrahydro-β-carbolines
    Shang, Hai
    Tian, Yu
    Luo, Jun
    Li, Lingyu
    Tang, Yefeng
    Zou, Zhongmei
    RSC ADVANCES, 2016, 6 (37): : 30835 - 30839
  • [3] Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles
    Duan, Shengguo
    Zhang, Wan
    Hu, Yuntong
    Xu, Ze-Feng
    Li, Chuan-Ying
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (17) : 3570 - 3575
  • [4] Synthesis of α-(2-Hydroxyphenyl)-α-Aminoketones by Rhodium-Catalyzed Tandem Reaction of 1-Sulfonyl-1,2,3-Triazoles and Benzoquinone-Derived Alcohols
    Xu, Ze-Feng
    Wang, Weipeng
    Cen, Mengjie
    Feng, Zijuan
    Duan, Shengguo
    Li, Chuan-Ying
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) : 2888 - 2893
  • [5] Catalyst-Free Synthesis of Polycyclic Spiroindolines by Cascade Reaction of 3-(2-Isocyanoethyl)indoles with 1-Sulfonyl-1,2,3-triazoles
    Chen, Cong
    Chen, Jing
    Wang, Han
    Xu, Ze-Feng
    Duan, Shengguo
    Li, Chuan-Ying
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13) : 9543 - 9553
  • [6] Synthesis of cyclobutane-fused dihydroazepines via rhodium-catalyzed intramolecular [4+3] cycloaddition of 1-sulfonyl-1,2,3-triazoles
    Wu, Zhaoqi
    Wang, Heng
    Chen, Tianci
    Xu, Ze-Feng
    Li, Chuan-Ying
    TETRAHEDRON LETTERS, 2023, 124
  • [7] Rhodium-Catalyzed Synthesis of 2,5-Epoxybenzo[f][1,4]oxazepines by Tandem Reaction of 1-Sulfonyl-1,2,3-triazoles and Salicylaldehydes
    Shi, Yinping
    Yu, Xing
    Li, Chuan-Ying
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (29) : 6429 - 6433
  • [8] Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with N-Sulfonyl 1,2,3-Triazoles
    Chuprakov, Stepan
    Kwok, Sen Wai
    Zhang, Li
    Lercher, Lukas
    Fokin, Valery V.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (50) : 18034 - +
  • [9] Asymmetric Synthesis of Cyclopropylmethanamines by Rhodium-catalyzed Cyclopropanation of Pinacol Allylboronate with N-Sulfonyl-1,2,3-triazoles
    Miura, Tomoya
    Nakamuro, Takayuki
    Nikishima, Hiroki
    Murakami, Masahiro
    CHEMISTRY LETTERS, 2016, 45 (08) : 1003 - 1005
  • [10] Rhodium-Catalyzed [4+2]-Annulation of o-Acylanilines with N-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines
    Rupa, Kavuri
    Yadagiri, Dongari
    Anbarasan, Pazhamalai
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13) : 9077 - 9086
12345