Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives

被引：2

作者：

Shu, Sai ^{[1
]}

Huang, Zhibin ^{[1
]}

Chen, Yujie ^{[1
]}

Yang, Shan ^{[1
]}

Jiang, Yaqiqi ^{[1
]}

Zhang, Jingyu ^{[1
]}

Zhao, Yingsheng ^{[1
,2
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Jiangsu, Peoples R China

[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453000, Henan, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 41卷 / 08期

基金：

中国国家自然科学基金;

关键词：

indoles; sulfoxonium ylides; cyclization; N-O BOND; CYCLIZATION; CASCADE; ACTIVATION; KETONES; ALKYNES;

D O I：

10.6023/cjoc202103027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(III)-catalyzed, regioselective C(2)-H activation/cyclization of N-methoxy-1H- indole-1-carboxamides and sulfoxonium ylides was developed. This novel synthetic procedure afforded dihydropyrimido[1,6-a]indol-1(2H)-ones in moderate to excellent yields. This reaction proceeds under simple and mild conditions with low catalyst loading and tolerates a wide range of substrates.

引用

页码：3171 / 3179

页数：9

共 50 条

[1] Catalytic Functionalization of Indoles in a New Dimension
Bandini, Marco
Eichholzer, Astrid
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9608 - 9644
[2] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds
Barday, Manuel
Janot, Christopher
Halcovitch, Nathan R.
Muir, James
Aissa, Christophe
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) : 13117 - 13121
[3] 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
[J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21): : 3688 - 3692
[4] Chen ZH, 2017, CHEM COMMUN, V53, P4258, DOI 10.1039/c7cc01201b
[5] Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides
Das, Riki
Kapur, Manmohan
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (02): : 1114 - 1126
[6] Chiral Phosphoric Acid-Catalyzed Asymmetric Cascade Reaction Of C(3) Substituted Indoles and Methyl Vinyl Ketone
Duan Dehe
Yin Qin
Wang Shouguo
Gu Qing
You Shuli
[J]. ACTA CHIMICA SINICA, 2014, 72 (09) : 1001 - 1004
[7] Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover
Guimond, Nicolas
Gouliaras, Christina
Fagnou, Keith
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) : 6908 - +
[8] REACTIONS WITH INDOLE-DERIVATIVES .47. AZA-EBURNAMONINE AND OXA-EBURNAMONINE
HAMMER, H
WINTERFELDT, E
[J]. TETRAHEDRON, 1981, 37 (21) : 3609 - 3613
[9] Design and Application of Indole-Based Allylic Donors for Pd-Catalyzed Decarboxylative Allylation Reactions
Hang, Qing-Qing
Liu, Si-Jia
Yu, Lei
Sun, Ting-Ting
Zhang, Yu-Chen
Mei, Guang-Jian
Shi, Feng
[J]. CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1612 - 1618
[10] Sulfoxonium Ylides as Carbene Precursors: Rhodium(III)-Catalyzed Sequential C-H Functionalization, Selective Enol Oxygen-Atom Nucleophilic Addition, and Hydrolysis
Huang, Yuanqiong
Lyu, Xueli
Song, Hongjian
Wang, Qingmin
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (22) : 5272 - 5276

← 1 2 3 4 5 →