Rh(III)-catalyzed C-H activation/intramolecular annulation for the synthesis of N-methoxydihydropyrimidin-2-one fused heterocycles

被引：1

作者：

Huang, Youchun ^{[1
]}

Kang, Ke ^{[1
]}

Zhong, Xiuwen ^{[1
]}

Yu, Yongping ^{[1
]}

Chen, Wenteng ^{[1
]}

机构：

[1] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2023年 / 115卷

关键词：

C -H activation; Intramolecular annulation; Rh(III)-catalyzed; N-Methoxydihydropyrimidin-2-one; CHEMODIVERGENT ANNULATIONS; REVERSE-TRANSCRIPTASE; SULFOXONIUM YLIDES; INHIBITION; ACTIVATION; INDOLES;

D O I：

10.1016/j.tetlet.2022.154311

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile rhodium-catalyzed C-H activation/intramolecular annulation strategy for N-methoxydihydropyrimidin-2-one was well realized in water media. Moreover, this Rh(III)-catalytic system facilitated the construction of N-methoxydihydropyrimidin-2-one scaffolds reminiscent of unnatural amino alcohols, transformation to pyran-2-one fused heterocycles as well as late-stage modification of drug molecules. Also, the protocol was easily scaled up to a gram-scale level. And H2O was proposed to act as an alternative coordination molecule to accelerate the generation of active Rh(III) catalyst species. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：6

共 50 条

[21] Synthesis of fused aromatic heterocycles by palladium-catalyzed C-H activation chemistry
Pacheco, Jarren
Knoerzer, Timm
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[22] Dual C-H activation: Rh(iii)-catalyzed cascade π-extended annulation of 2-arylindole with benzoquinone
Zhang, Qijing
Li, Qianrong
Wang, Chengming
RSC ADVANCES, 2021, 11 (21) : 13030 - 13033
[23] Synthesis of indene-fused spiro-dibenz(ox)azepines via Rh(iii)-catalyzed cascade regioselective C-H activation/annulation
Naskar, Koushik
Karmakar, Sudip
Mondal, Imtiaj
Sarkar, Writhabrata
Roy, Shantonu
Roy, Anupam
Deb, Indubhusan
CHEMICAL COMMUNICATIONS, 2023, 59 (50) : 7751 - 7754
[24] One-Pot Rh(III)-Catalyzed Twofold C-H Activation/Oxidative Annulation of N-Arylpyrroles with Alkynes to Fluorescent Ullazines
Otero-Riesgo, Sergio
Varela, Jesus A.
Saa, Carlos
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) : 2312 - 2323
[25] Rh(III)-Catalyzed C-H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones
Shu, Bing
Song, Jia-Lin
Chen, Shao-Yong
Zheng, Yi-Chuan
Zhang, Shang-Shi
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06): : 3499 - 3508
[26] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
Kumar, Sanjeev
Nunewar, Saiprasad
Usama, Khan Mohammad
Kanchupalli, Vinaykumar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
[27] Three-Component Synthesis of Isoquinolone Derivatives via Rh(III)-Catalyzed C-H Activation and Tandem Annulation
Yang, Zhenke
Liu, Jidan
Li, Yuting
Ding, Jiawen
Zheng, Liyao
Liu, Zhao-Qing
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14809 - 14818
[28] N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C-H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes
Villar, Jose M.
Suarez, Jaime
Varela, Jesus A.
Saa, Carlos
ORGANIC LETTERS, 2017, 19 (07) : 1702 - 1705
[29] Rh(III)-Catalyzed C-H Annulation of N-Nitrosoanilines with Iodonium Ylides for the Synthesis of N-Alkyl Indoles
Liu, Chaoshui
Dai, Qiuzi
Li, Yaqian
Huang, Chuhan
Guo, Lijuan
Yang, Zi
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 7281 - 7289
[30] Rhodium-catalyzed intramolecular annulation via C-H activation leading to fused tricyclic indole scaffolds
Tao, Pengyu
Jia, Yanxing
CHEMICAL COMMUNICATIONS, 2014, 50 (55) : 7367 - 7370

← 1 2 3 4 5 →