Direct synthesis of indazole derivatives via Rh(iii)-catalyzed C-H activation of phthalazinones and allenes

被引：15

作者：

Yin, Chuanliu ^{[1
]}

Zhong, Tianshuo ^{[1
]}

Zheng, Xiangyun ^{[1
]}

Li, Lianghao ^{[1
]}

Zhou, Jian ^{[1
]}

Yu, Chuanming ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 35期

基金：

中国国家自然科学基金;

关键词：

4+1 ANNULATION; FUNCTIONALIZATION; ALKALOIDS; CINNOLINES; AMIDES; SEEDS;

D O I：

10.1039/d1ob01458g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Rh(iii)-catalyzed annulation of phthalazinones or pyridazinones with various allenes was developed, leading to the formation of indazole derivatives bearing a quaternary carbon in moderate to good yields. The targeted products were synthesized via sequential C-H activation and olefin insertion, followed by beta-hydride elimination and intramolecular cyclization. The synthetic protocol proceeded efficiently with broad functional group tolerance, high atom efficiency and high Z-selectivity. The practicability of this method was proved by synthetic transformation.

引用

页码：7701 / 7705

页数：5

共 50 条

[21] Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates via C-H Bond Activation
Gadakh, Sunita K.
Dey, Soumen
Sudalai, Arumugarn
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (22) : 11544 - 11550
[22] Transition-metal-catalyzed C-H bond activation/functionalization and annulation of phthalazinones
Sivaraj, Chandrasekaran
Ramkumar, Alagumalai
Sankaran, Nagesh
Gandhi, Thirumanavelan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (38) : 8165 - 8183
[23] Synthesis of CF3-Containing Spiro-[Indene-Proline] Derivatives via Rh(III)-Catalyzed C-H Activation/Annulation
Bubnova, Alexandra S.
Vorobyeva, Daria V.
Godovikov, Ivan A.
Smol'yakov, Alexander F.
Osipov, Sergey N.
MOLECULES, 2023, 28 (23):
[24] Rh(III)-Catalyzed Synthesis of 2-Nitro-2H -azirines via sp3 C-H Activation
Huang, Xiaojun
Ge, Yun
Qian, Yang
Zhang, Zhengyu
SYNLETT, 2022, 33 (10) : 969 - 972
[25] Construction of Peptide-Isoquinolone Conjugates via Rh(III)- Catalyzed C-H Activation/Annulation
Song, Liangliang
Lv, Zhenwei
Li, Yan
Zhang, Kui
Van der Eycken, Erik V.
Cai, Lingchao
ORGANIC LETTERS, 2023, 25 (17) : 2996 - 3000
[26] Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides
Xu, Youwei
Yang, Xifa
Zhou, Xukai
Kong, Lingheng
Li, Xingwei
ORGANIC LETTERS, 2017, 19 (16) : 4307 - 4310
[27] Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation
Semakul, Natthawat
Jackson, Kelvin E.
Paton, Robert S.
Rovis, Tomislav
CHEMICAL SCIENCE, 2017, 8 (02) : 1015 - 1020
[28] Synthesis of Tetrahydrocarbazol-4-ones via Rh(III)-Catalyzed C-H Activation/Annulation of Arylhydrazines with Iodonium Ylidesb
Li, He
Gu, Haichun
Lu, Ye
Xu, Ning
Han, Narenchaoketu
Li, Jiaqi
Liu, Jinghai
Liu, Jinglin
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (12) : 8142 - 8150
[29] Rh(III)-Catalyzed C-H Activation and Double Directing Group Strategy for the Regioselective Synthesis of Naphthyridinones
Huckins, John R.
Bercot, Eric A.
Thiel, Oliver R.
Hwang, Tsang-Lin
Bio, Matthew M.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) : 14492 - 14495
[30] Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C-H activation and annulation of sulfoxonium ylides with dioxazolones
Yu, Yongqi
Xia, Zhen
Wu, Qianlong
Liu, Da
Yu, Lin
Xiao, Yuanjiu
Tan, Ze
Deng, Wei
Zhu, Gangguo
CHINESE CHEMICAL LETTERS, 2021, 32 (03) : 1263 - 1266

← 1 2 3 4 5 →