Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes

被引:5
|
作者
Liu, Yan-Zhi [1 ]
Zeng, Yao-Fu [3 ]
Wei, Jiaohang [1 ]
Xiao, Lin [1 ]
Shu, Bing [2 ]
Song, Jia-Lin [1 ]
Zou, Wen-Xuan [1 ]
Shen, Dan-Ting [1 ]
Chen, Shao-Yong [1 ]
Zheng, Yi-Chuan [1 ]
Zhang, Shang-Shi [1 ]
机构
[1] Guangdong Pharmaceut Univ, Ctr Drug Res & Dev, Guangdong Prov Engn Ctr Top Precise Drug Delivery, Guangdong Prov Key Lab Adv Drug Delivery, R China, Guangzhou 510006, Peoples R China
[2] Guangdong Pharmaceut Univ, Sch Pharm, Guangzhou 510006, Peoples R China
[3] Univ South China, Sch Pharmaceut Sci, Hunan Prov Key Lab Tumor Microenvironm Respons Dru, Hengyang 421001, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ACTIVATION; CATALYZED DENITROGENATIVE ANNULATION; ALKYNE INSERTION; METHYLENECYCLOPROPANES; BENZOTRIAZINONES; HYDROARYLATIONS;
D O I
10.1021/acs.orglett.3c01596
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rh (III)-catalyzed dienylation and cyclopropylation of1,2,3-benzotriazinoneswith alkylidenecyclopropanes (ACPs) has been achieved. Different fromthe previous reports of 1,2,3-benzotriazinones, the triazinone ringremained intact in this C-H bond functionlization reaction.Also, the denitrogenative cyclopropylation could also be realizedby changing the reaction temperature. This protocol is featured withhigh E selectivity, wide substrate scope, and divergentstructures of products.
引用
收藏
页码:5179 / 5184
页数:6
相关论文
共 50 条
  • [1] Rh(iii)-Catalyzed dienylation and cyclopropylation of indoles at the C4 position with alkylidenecyclopropanes
    Liu, Yan-Zhi
    Zeng, Yao-Fu
    Shu, Bing
    Zheng, Yi-Chuan
    Xiao, Lin
    Chen, Shao-Yong
    Song, Jia-Lin
    Zhang, Xuanxuan
    Zhang, Shang-Shi
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (16): : 4287 - 4293
  • [2] Rh(III)-Catalyzed Selective C-H Alkylation and Alkenylation of 1,2,3-Benzotriazinones with Maleimides
    Xiao, Lin
    Shen, Dan-Ting
    Zou, Wen-Xuan
    Song, Jia-Lin
    Wei, Jiaohang
    Liu, Xiang
    Zhang, Shang-Shi
    Zhang, Luyong
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (17) : 3646 - 3652
  • [3] Recent advances in synthesis and transformations of 1,2,3-benzotriazinones
    Doraghi, Fatemeh
    Karimian, Somaye
    Larijani, Bagher
    Mahdavi, Mohammad
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2024, 1013
  • [4] Ru(II)-Catalyzed C-H Amination of 1,2,3-Benzotriazinones with Azide Compounds
    Wang, Hanchi
    Luo, Quanjian
    Li, Jin-Heng
    Sun, Bo
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (17): : 12249 - 12254
  • [5] A Novel Synthesis of 1,2,3-Benzotriazinones from 2-(o-Aminophenyl)oxazolines
    Rocha-Alonzo, Fernando
    Chavez, Daniel
    Ochoa-Teran, Adrian
    Morales-Morales, David
    Velazquez-Contreras, Enrique F.
    Parra-Hake, Miguel
    JOURNAL OF CHEMISTRY, 2017, 2017
  • [6] Synthesis of lsoquinolones Using Visible-Light-Promoted Denitrogenative Alkyne Insertion of 1,2,3-Benzotriazinones
    Wang, Hao
    Yu, Shouyun
    ORGANIC LETTERS, 2015, 17 (17) : 4272 - 4275
  • [7] Electrochemical annulation of 1,2,3-benzotriazinones with alkynes to access isoquinolin-1(2H)-ones
    Chen, Jinkang
    Xiao, Linxia
    Qi, Liang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (36) : 7295 - 7299
  • [8] APPROACHES TO SYNTHESIS OF QUINAZOLINO[1,2,3]BENZOTRIAZINONES
    AHERN, TP
    FONG, H
    VAUGHAN, K
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (02): : 290 - 296
  • [9] Rh(III)-catalyzed, 1,2,3-triazole-assisted directed C-H coupling with diazo diphosphonates
    Yu, Zhu-Jun
    Zhang, Chen
    Li, Jiang-Lian
    Liu, Yan-Zhao
    Yu, Xin-Ling
    Guo, Li
    Li, Guo-Bo
    Wu, Yong
    TETRAHEDRON LETTERS, 2018, 59 (29) : 2816 - 2819
  • [10] Rh(III)-Catalyzed Chemodivergent Coupling of N-Phenoxyacetamides and Alkylidenecyclopropanes via C-H Activation
    Xu, Guiqing
    Chen, Qi
    Wu, Fen
    Bai, Dachang
    Chang, Junbiao
    Li, Xingwei
    ORGANIC LETTERS, 2021, 23 (08) : 2927 - 2932