Copper-Promoted Direct Decarboxylative C3-Acylation of Electron-Rich Indolizines Using α-Keto Acids

被引：1

作者：

Liu, Hao ^{[1
]}

Ren, Shaohong ^{[1
]}

Ma, Chuanjun ^{[1
]}

Shi, Guowei ^{[1
]}

Li, Yongchao ^{[1
]}

Duan, Guiyun ^{[1
]}

Ge, Yanqing ^{[1
]}

机构：

[1] Shandong First Med Univ & Shandong Acad Med Sci, Dept Chem & Pharmaceut Engn, 619 Changcheng Rd, Tai An 271016, Shandong, Peoples R China

来源：

CHEMISTRYSELECT | 2022年 / 7卷 / 21期

关键词：

Acylation; C-H activation; Decarboxylation; Indolizine; alpha-Keto acids; RATIOMETRIC FLUORESCENT-PROBE; ORTHO-ACYLATION; OXOCARBOXYLIC ACIDS; SO2; DERIVATIVES; FRET SYSTEM; ARYLATION; INDOLES; CATALYSIS; CU2+; HG2+;

D O I：

10.1002/slct.202104426

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

C-3 substituted indolizines are important biological heterocycles and luminescent molecules. The development of new methods for direct arylation of indolizines is highly desired. Herein, the C3-acylation of electron-rich indolizines with alpha-keto acids through Cu-promoted decarboxylation was descried. Under this simple reaction conditions, a variety of indolizine derivatives were synthesized and characterized. The structure of product 3 a was confirmed in an X-ray crystal analysis. In addition, the mechanism was also proposed.

引用

页数：5

共 17 条

[1] Copper-promoted decarboxylative direct C3-acylation of N-substituted indoles with α-oxocarboxylic acids
Yu, Lin
Li, Pinhua
Wang, Lei
CHEMICAL COMMUNICATIONS, 2013, 49 (23) : 2368 - 2370
[2] Copper-catalyzed decarboxylative C3-acylation of free (N-H) indoles with α-oxocarboxylic acids
Wang, Cuiping
Wang, Shaoyan
Li, Hua
Yan, Jingbo
Chi, Haijun
Chen, Xichao
Zhang, Zhiqiang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (11) : 1721 - 1724
[3] Palladium-catalyzed decarboxylative C3-acylation of benzofurans and benzothiophenes with α-oxocarboxylic acids via direct sp2 C-H bond activation
Gong, Wei-Jie
Liu, De-Xian
Li, Fei-Long
Gao, Jun
Li, Hong-Xi
Lang, Jian-Ping
TETRAHEDRON, 2015, 71 (08) : 1269 - 1275
[4] Photoinduced Copper-Promoted Decarboxylative Trifluoromethylselenolation of Aromatic Carboxylic Acids with [Me4N][SeCF3]
Liu, Lei
Gu, Yu-Cheng
Zhang, Cheng-Pan
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 9372 - 9380
[5] Copper/Persulfate-Promoted Oxidative Decarboxylative C-H Acylation of Pyrazolones with α-Oxocarboxylic Acids: Direct Access to 4-Acylpyrazolones under Mild Conditions
Kittikool, Tanakorn
Thupyai, Akkharaphong
Phomphrai, Khamphee
Yotphan, Sirilata
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (17) : 3345 - 3355
[6] Bronsted acidic ionic liquid-promoted direct C3-acylation of N-unsubstituted indoles with acid anhydrides under microwave irradiation
Phuong Hoang Tran
Anh-Thanh Duy Nguyen
Hai Truong Nguyen
Thach Ngoc Le
RSC ADVANCES, 2017, 7 (86) : 54399 - 54406
[7] Dehydrogenative Synthesis of C3-Azolylindoles via Copper-Promoted Annulative Direct Coupling of o-Alkynylanilines
Oda, Yoshiro
Matsuyama, Naoto
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
SYNTHESIS-STUTTGART, 2012, 44 (10): : 1515 - 1520
[8] Copper-Promoted Direct C-H Amination of Benzothiazoles Using Formamides as Nitrogen Sources: An Efficient Approach for Synthesis of 2-Aminothiazoles
Yu, Mengxuan
Wang, Biying
Zhou, Peng
Jia, Xiaodong
Yuan, Yu
CHEMISTRYSELECT, 2016, 1 (19): : 6217 - 6220
[9] Alkene Diamination Using Electron-Rich Amines: Hypervalent Iodine-Promoted Inter-/Intramolecular C-N Bond Formation
Hong, Ki Bum
Johnston, Jeffrey N.
ORGANIC LETTERS, 2014, 16 (14) : 3804 - 3807
[10] Transition-metal-free direct trifluoromethylthiolation of electron-rich aromatics using CF3SO2Na in the presence of PhPCl2
Zhao, Xia
Zheng, Xiancai
Tian, Miaomiao
Sheng, Jianqiao
Tong, Yifan
Lu, Kui
TETRAHEDRON, 2017, 73 (51) : 7233 - 7238

← 1 2 →