Cobalt-Catalyzed Cyclization of 2-Bromobenzamides with Carbodiimides: A New Route for the Synthesis of 3-(Imino)isoindolin-1-ones

被引：2

作者：

Aman, Hasil ^{[1
]}

Huang, Yu-Chiao ^{[1
]}

Liu, Yu-Hao ^{[1
]}

Tsai, Yu-Lin ^{[2
]}

Kim, Min ^{[3
]}

Hsieh, Jen-Chieh ^{[2
]}

Chuang, Gary Jing ^{[1
]}

机构：

[1] Chung Yuan Christian Univ, Dept Chem, Taoyuan 320314, Taiwan

[2] Tamkang Univ, Dept Chem, New Taipei 251301, Taiwan

[3] Chungbuk Natl Univ, Dept Chem, Cheongju 28644, South Korea

来源：

MOLECULES | 2021年 / 26卷 / 23期

关键词：

cobalt-catalyzed; N-heterocycle; cyclization; carbodiimide; 3-(imino)isoindolin-1-one; N-H BONDS; C-H; EFFICIENT SYNTHESIS; ANNULATION; BENZAMIDES; ALKYNES; PHTHALALDEHYDE; ANALOGS;

D O I：

10.3390/molecules26237212

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A novel synthetic pathway to approach 3-(imino)isoindolin-1-ones by the Co-catalyzed cyclization reaction of 2-bromobenzamides with carbodiimides has been developed. This catalytic reaction can tolerate a variety of substituents and provide corresponding products in moderate yields for most cases. According to the literature, the reaction mechanism is proposed through the formation of a five-membered aza-cobalacycle complex, which carries out the following reaction subsequence, including nucleophilic addition and substitution, to furnish the desired structures.

引用

页数：9

共 35 条

[1] Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds
Ackermann, Lutz
Lygin, Alexander V.
Hofmann, Nora
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) : 6379 - 6382
[2] Iron-catalyzed C-H/N-H activation by triazole guidance: versatile alkyne annulation
Cera, G.
Haven, T.
Ackermann, L.
[J]. CHEMICAL COMMUNICATIONS, 2017, 53 (48) : 6460 - 6463
[3] Cobalt-catalyzed electrochemical C-H/N-H functionalization of N-(quinolin-8-yl)benzamide with isocyanides
Chen, Jinkang
Jin, Licheng
Zhou, Jian
Jiang, Xinpeng
Yu, Chuanming
[J]. TETRAHEDRON LETTERS, 2019, 60 (31) : 2054 - 2058
[4] Controlled Synthesis of Enantioselective 1-Aminoindenes via Cobalt-Catalyzed [3+2] Annulation Reaction
Chen, Min-Hsien
Hsieh, Jen-Chieh
Lee, Yi-Hsien
Cheng, Chien-Hong
[J]. ACS CATALYSIS, 2018, 8 (10): : 9364 - 9369
[5] Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-H-Phenanthridines via a Transition-Metal-Free Process
Chen, Wei-Lin
Chen, Chun-Yuan
Chen, Yan-Fu
Hsieh, Jen-Chieh
[J]. ORGANIC LETTERS, 2015, 17 (06) : 1613 - 1616
[6] An efficient synthesis of (NH)-phenanthridinones via ligand-free copper-catalyzed annulation
Chen, Yan-Fu
Wu, Yi-Sheng
Jhan, Yu-Huei
Hsieh, Jen-Chieh
[J]. ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (03): : 253 - 257
[7] Synthesis of Polysubstituted Phenanthridines via Ligand-Free Copper-Catalyzed Annulation
Chen, Yan-Fu
Hsieh, Jen-Chieh
[J]. ORGANIC LETTERS, 2014, 16 (17) : 4642 - 4645
[8] Synthesis of phenanthridine skeletal Amaryllidaceae alkaloids
Fan-Chiang, Tai-Ting
Wang, Hung-Kai
Hsieh, Jen-Chieh
[J]. TETRAHEDRON, 2016, 72 (36) : 5640 - 5645
[9] Nickel-Catalyzed Oxidative C-H/N-H Isocyanide Insertion: An Efficient Synthesis of Iminoisoindolinone Derivatives
Hao, Wenyan
Tian, Jun
Li, Wu
Shi, Renyi
Huang, Zhiliang
Lei, Aiwen
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (11) : 1664 - 1667
[10] Synthesis of N-Heterocycles via Transition-Metal-Catalyzed Tandem Addition/Cyclization of a Nitrile
Hsieh, Jen-Chieh
Su, Haw-Lih
[J]. SYNTHESIS-STUTTGART, 2020, 52 (06): : 819 - 833

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