Hypervalent iodine(iii) promoted C-H/C-H amination/annulation tandem reactions: synthesis of benzimidazoles from simple anilines and aldehydes

被引：6

作者：

Long, Lipeng ^{[1
]}

Li, Xin ^{[1
]}

Tu, Mengshi ^{[1
]}

Zhang, Yekun ^{[1
]}

Qiao, Liang ^{[1
]}

Luo, Wenjun ^{[1
]}

Chen, Zhengwang ^{[1
]}

机构：

[1] Gannan Normal Univ, Key Lab Organo Pharmaceut Chem Jiangxi Prov, Ganzhou 341000, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 02期

关键词：

CATALYZED REGIOSPECIFIC SYNTHESIS; ONE-POT SYNTHESIS; OXIDATIVE ANNULATION; BOND FORMATION; DERIVATIVES; ROUTE; FUNCTIONALIZATION; CYCLIZATION; CHEMISTRY; ARYLATION;

D O I：

10.1039/d2qo01644c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel hypervalent iodine mediated cascade transformation of anilines and aldehydes to benzimidazoles was developed. A series of 1,2-disubstituted benzimidazoles were achieved with aromatic, heteroaromatic, and aliphatic aldehydes. In this procedure, the initial condensation of anilines with aldehydes afforded N-arylimine intermediates which underwent C-H/C-H amination/annulation to generate the desired products in moderate to excellent yields. This reaction is an extremely simple reaction system with good functional group tolerance, and water is the only byproduct formed.

引用

页码：473 / 479

页数：7

共 50 条

[31] Metallaphotocatalytic synthesis of anilines through tandem C-N transposition and C-H alkylation of alkylamines
Zhang, Zhong-Wei
Feng, Zhe
Ma, Jun-An
Cheung, Chi Wai
NATURE SYNTHESIS, 2023, 2 (12): : 1171 - 1183
[32] Sequential Allylic C-H Amination/Vinylic C-H Arylation: A Strategy for Unnatural Amino Acid Synthesis from α-Olefins
Jiang, Chao
Covell, Dustin J.
Stepan, Antonia F.
Plummer, Mark S.
White, M. Christina
ORGANIC LETTERS, 2012, 14 (06) : 1386 - 1389
[33] Synthesis of Tetramic Acid Derivatives via Intramolecular sp3 C-H Amination Mediated by Hypervalent Iodine(III) Reagents/Bronsted Acids
Mao, Lujia
Li, Yan
Xiong, Tao
Sun, Kai
Zhang, Qian
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02): : 733 - 737
[34] N-Acylsulfonamide Assisted Tandem C-H Olefination/Annulation: Synthesis of Isoindolinones
Zhu, Chen
Falck, J. R.
ORGANIC LETTERS, 2011, 13 (05) : 1214 - 1217
[35] Copper mediated C-H amination with oximes: en route to primary anilines
Xu, Lin-Lin
Wang, Xing
Ma, Biao
Yin, Ming-Xing
Lin, Hai-Xia
Dai, Hui-Xiong
Yu, Jin-Quan
CHEMICAL SCIENCE, 2018, 9 (23) : 5160 - 5164
[36] N-Acylsulfonamide assisted tandem C-H olefination/annulation: Synthesis of isoindolinones
Zhu, Chen
Falck, J. R.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[37] Hypervalent iodine mediated C-H amination of quinoxalinones with heteroaromatic amines under metal-free conditions
Han, Qing-Qing
Chen, De-Mao
Wang, Zu-Li
Sun, Yuan-Yuan
Yang, Shao-Hui
Song, Jing-Cheng
Dong, Dao-Qing
CHINESE CHEMICAL LETTERS, 2021, 32 (08) : 2559 - 2561
[38] Palladium nanomaterials in catalytic intramolecular C-H amination reactions
Chng, Leng Leng
Yang, Jun
Wei, Yifeng
Ying, Jackie Y.
CHEMICAL COMMUNICATIONS, 2014, 50 (65) : 9049 - 9052
[39] Catalytic insertion reactions for the amination of C-H bonds.
DuBois, J
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U46 - U46
[40] Copper catalyzed benzylic C-H amination using simple amination reagents
Wang, Anqi
Emmert, Marion
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250

← 1 2 3 4 5 →