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

被引:17
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
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
收藏
页码:7701 / 7705
页数:5
相关论文
共 43 条
[1]   Synthesis and antiinflammatory activity of novel indazolones [J].
Abouzid, KAM ;
El-Abhar, HS .
ARCHIVES OF PHARMACAL RESEARCH, 2003, 26 (01) :1-8
[2]  
Asif Mohammad, 2015, Mini Rev Med Chem, V14, P1093
[3]   An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles [J].
Baumann, Marcus ;
Baxendale, Ian R. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :2265-2319
[4]   Co(III)-Catalyzed [4+1] Annulation of Amides with Allenes via C-H Activation [J].
Boobalan, Ramadoss ;
Santhoshkumar, Rajagopal ;
Cheng, Chien-Hong .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) :1140-1145
[5]   The synthesis of a selective PDE4/TNFα inhibitor [J].
Caron, S ;
Vazquez, E .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (06) :587-592
[6]   Cobalt(II)-Catalyzed C-H/N-H Functionalization and Annulation of N-(quinolin-8-yl)benzamide with Cyclopropanols [J].
Chen, Jinkang ;
Yin, Chuanliu ;
Zhou, Jian ;
Yu, Chuanming .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (06) :915-923
[7]   Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4-a]indolone and Dihydropyrimido [1,6-a]indolone via Rh(III)-catalyzed [3+3] or [4+2] C-H Annulation [J].
Chen, Junyu ;
Zhong, Tianshuo ;
Zheng, Xiangyun ;
Yin, Chuanliu ;
Zhang, Lei ;
Zhou, Jian ;
Jiang, Xinpeng ;
Yu, Chuanming .
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) :446-452
[8]   Divergent Synthesis of Tunable Cyclopentadienyl Ligands and Their Application in Rh-Catalyzed Enantioselective Synthesis of Isoindolinone [J].
Cui, Wen-Jun ;
Wu, Zhi-Jie ;
Gu, Qing ;
You, Shu-Li .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (16) :7379-7385
[9]   Indazole estrogens:: Highly selective ligands for the estrogen receptor β [J].
De Angelis, M ;
Stossi, F ;
Carlson, KA ;
Katzenellenbogen, BS ;
Katzenellenbogen, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) :1132-1144
[10]   A POTENT, ORALLY-ACTIVE, BALANCED AFFINITY ANGIOTENSIN-II AT(1) ANTAGONIST AND AT(2) BINDING INHIBITOR [J].
DELASZLO, SE ;
QUAGLIATO, CS ;
GREENLEE, WJ ;
PATCHETT, AA ;
CHANG, RSL ;
LOTTI, VJ ;
CHEN, TB ;
SCHECK, SA ;
FAUST, KA ;
KIVLIGHN, SS ;
SCHORN, TS ;
ZINGARO, GJ ;
SIEGL, PKS .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (21) :3207-3210