The Pyridotriazole Works as a Traceless Directing Group: A C-H Activation/Annulation Cascade Reaction with Iodonium Ylides

被引：11
|
作者：
Lv, Guanghui [1 ,2 ]
Zhang, Qingyao [1 ]
Zhang, Cuimei [1 ]
Chen, Yuting [1 ]
Lin, Zheng [1 ]
Lai, Ruizhi [1 ]
Yang, Zhongzhen [1 ]
Wu, Yong [1 ]
机构：
[1] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Key Lab Drug Targeting, Chengdu 610041, Sichuan, Peoples R China
[2] Hubei Univ Med, Taihe Hosp, Dept Pharm, Shiyan 442000, Hubei, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 22期
关键词：
CATALYZED DENITROGENATIVE TRANSANNULATION; ACTIVATION; ACCESS; ALKYNES; ANHYDROEXFOLIAMYCIN; REARRANGEMENT; METABOLITE; CARBENES; NITRONES; ARYL;
D O I：
10.1021/acs.orglett.3c01102
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel Rh-catalyzed cascade reaction of pyridotriazoleswith iodoniumylides is reported. This one-pot procedure involves a triazole-directed ortho-position C-H carbene insertion, followed byintramolecular denitrogenation annulation. It was noteworthy thatthis reaction provided straightforward access to 1H-isochromene frameworks with excellent yields (up to 94% yield).
引用
收藏
页码：4022 / 4027
页数：6
相关论文
共 50 条
  • [21] A removable directing group-assisted Rh(iii)-catalyzed direct C-H bond activation/annulation cascade to synthesize highly fused isoquinolines
    Cheng, Yilang
    Han, Xu
    Li, Junyou
    Zhou, Yu
    Liu, Hong
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (20): : 3186 - 3192
  • [22] Rh(III)-Catalyzed C-H Activation/Annulation of N-Methyl Arylhydrazines with Iodonium Ylides toward Ring-fused Cinnolines
    Pan, Changduo
    Yuan, Cheng
    Chen, Dongdong
    Chen, Yuefeng
    Yu, Jin-Tao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (02)
  • [23] Aldehyde as a Traceless Directing Group for Regioselective C-H Alkylation Catalyzed by Rhodium(III) in Air
    Chen, Si-Qi
    Li, Xin-Ran
    Li, Chao-Jun
    Fan, Juan
    Liu, Zhong-Wen
    Shi, Xian-Ying
    ORGANIC LETTERS, 2020, 22 (04) : 1259 - 1264
  • [24] Ru(ii)-Catalyzed C-H bond activation/annulation of N-iminopyridinium ylides with sulfoxonium ylides
    Li, Xiang
    Li, Danlu
    Zhang, Xiaofei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (07) : 1475 - 1479
  • [25] Iodonium ylides: an emerging and alternative carbene precursor for C-H functionalizations
    Kumar, Sanjeev
    Borkar, Vaishnavi
    Mujahid, Mohd.
    Nunewar, Saiprasad
    Kanchupalli, Vinaykumar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 21 (01) : 24 - 38
  • [26] Traceless directing groups: a novel strategy in regiodivergent C-H functionalization
    Rani, Geetika
    Luxami, Vijay
    Paul, Kamaldeep
    CHEMICAL COMMUNICATIONS, 2020, 56 (83) : 12479 - 12521
  • [27] Directing group assisted meta-hydroxylation by C-H activation
    Maji, Arun
    Bhaskararao, Bangaru
    Singha, Santanu
    Sunoj, Raghavan B.
    Maiti, Debabrata
    CHEMICAL SCIENCE, 2016, 7 (05) : 3147 - 3153
  • [28] Rh(III)-Catalyzed Synthesis of Isocoumarins via C-H Activation of Phenacyl Phosphoniums with Iodonium Ylides
    Jiang, Lu
    Gao, Lei
    Li, Xiaofei
    Shao, Tingting
    Yao, Jinzhong
    Miao, Maozhong
    Zhou, Hongwei
    SYNTHESIS-STUTTGART, 2024, 56 (01): : 47 - 54
  • [29] A directing group switch in copper-catalyzed electrophilic C-H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole
    Begam, Hasina Mamataj
    Nandi, Shantanu
    Jana, Ranjan
    CHEMICAL SCIENCE, 2022, 13 (19) : 5726 - 5733
  • [30] Rh(iii)-Catalyzed C-H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones
    Cai, Libo
    Zhu, Xiaoyi
    Chen, Jiayi
    Lin, Aijun
    Yao, Hequan
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21): : 3688 - 3692
12345