Rhodium(III)-Catalyzed C-H Activation/[5+2] Cascade Annulation of Aroyl Hydrazides with Iodonium Ylides for the Synthesis of Seven-Membered Dibenzodiazepinediones

被引：2

作者：

Li, He ^{[1
]}

Chen, Tao ^{[1
]}

Wang, Zhiwei ^{[1
]}

Li, Yuxin ^{[1
]}

Lu, Ye ^{[2
]}

Jin, Xinxin ^{[1
]}

Xu, Ning ^{[1
]}

Liu, Jinglin ^{[1
]}

机构：

[1] Inner Mongolia Minzu Univ, Coll Chem & Mat Sci, Inner Mongolia Key Lab Nat Prod Chem & Funct Mol S, Innovat Team Opt Funct Mol Devices, Tongliao 028000, Peoples R China

[2] Inner Mongolia Minzu Univ, Nano Innovat Inst NII, Coll Chem & Mat Sci, Inner Mongolia Key Lab Carbon Nanomat, Tongliao 028000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 18期

关键词：

N-PHENOXYACETAMIDES; FUNCTIONALIZATION; ACTIVATION/ANNULATION; SULFOXIMINES; ALKYLATION; ACTIVATION; STRATEGY;

D O I：

10.1021/acs.joc.4c01557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Rh(III)-catalyzed C-H activation/[5 + 2] cascade annulation of aroyl hydrazides with iodonium ylides is accomplished, in which diverse seven-membered dibenzodiazepinediones were afforded in moderate to excellent yields. This annulation reaction features an ideal functional group tolerance and a wide substrate scope. Large-scale and derivatization reactions were conducted to demonstrate the potential utility of this transformation.

引用

页码：13412 / 13417

页数：6

共 49 条

[1] 1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds [J].

Akter, Monalisa ;

Rupa, Kavuri ;

Anbarasan, Pazhamalai .

CHEMICAL REVIEWS, 2022, 122 (15) :13108-13205

[2] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds [J].

Barday, Manuel ;

Janot, Christopher ;

Halcovitch, Nathan R. ;

Muir, James ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13117-13121

[3] The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings [J].

Battiste, MA ;

Pelphrey, PM ;

Wrightthl, DL .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) :3438-3447

[4] Sulfoxonium ylides: simple compounds with chameleonic reactivity [J].

Bisag, Giorgiana Denisa ;

Ruggieri, Silvia ;

Fochi, Mariafrancesca ;

Bernardi, Luca .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (43) :8793-8809

[5] Metal-catalyzed B-H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums [J].

Cao, Hou-Ji ;

Wei, Xing ;

Sun, Fangxiang ;

Zhang, Xiaolei ;

Lu, Changsheng ;

Yan, Hong .

CHEMICAL SCIENCE, 2021, 12 (47) :15563-15571

[6] Rh(III)-Catalyzed C-H Activation/Cycloisomerization of N-Phenoxyacetamides with Enynones for One-Pot Assembly of Furylated 2-Alkenylphenols [J].

Chen, Weijie ;

Liu, Fu-Xiaomin ;

Bian, Mengyao ;

Li, Liping ;

Zhou, Zhi ;

Yi, Wei .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23) :15557-15566

[7] Cp*RhIII-Catalyzed Sulfonamide-Directed Ortho Arene C-H Carbenoid Functionalization with Pyridotriazoles [J].

Dong, Yi ;

Chen, Jiajing ;

Cui, Yunjian ;

Bao, Liangliang ;

Xu, Heng .

ORGANIC LETTERS, 2020, 22 (03) :772-775

[8] Rh(iii)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds [J].

Ghosh, Bidhan ;

Samanta, Rajarshi .

CHEMICAL COMMUNICATIONS, 2019, 55 (48) :6886-6889

[9] Rh(iii)-Catalyzed C(sp2)-H functionalization/cyclization cascade of N-carboxamide indole and iodonium reagents for access to indoloquinazolinone derivatives [J].

Han, Zhi-Peng ;

Xu, Meng-Meng ;

Zhang, Rui-Ying ;

Xu, Xiao-Ping ;

Ji, Shun-Jun .

GREEN CHEMISTRY, 2021, 23 (17) :6337-6340

[10] Recent advances in transition-metal-catalyzed carbene insertion to C-H bonds [J].

He, Yuan ;

Huang, Zilong ;

Wu, Kaikai ;

Ma, Juan ;

Zhou, Yong-Gui ;

Yu, Zhengkun .

CHEMICAL SOCIETY REVIEWS, 2022, 51 (07) :2759-2852

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