NHC-Catalyzed Tandem Reaction: A Strategy for the Synthesis of 2-Pyrrolidinone-Functionalized Phenanthridines

被引：7

作者：

Zhou, Nengneng ^{[1
]}

Wang, Lei ^{[1
]}

Zhao, Fangli ^{[1
]}

Gao, Xiang ^{[1
]}

Zhao, Xiaowei ^{[1
]}

Zhang, Man ^{[1
]}

机构：

[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Functionalized Mol Solids, Minist Educ,Anhui Key Lab Mol Based Mat, Wuhu 241000, Anhui, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 23期

基金：

中国国家自然科学基金;

关键词：

RADICAL C-P; 6-PHOSPHORYLATED PHENANTHRIDINES; METAL-FREE; CYCLIZATION; 2-ISOCYANOBIPHENYLS; ISOCYANIDES; DERIVATIVES; BASE;

D O I：

10.1021/acs.joc.3c02086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, an N-heterocyclic carbene (NHC)-catalyzed tandem cyclization/addition/cyclization reaction of 2-isocyanobiaryls and alpha-bromo-N-cinnamylamides for the synthesis of 2-pyrrolidinone-functionalized phenanthridines is developed. This protocol features a radical cascade process, broad substrate scope, and good functional group compatibility under metal- and oxidant-free reaction conditions.

引用

页码：16556 / 16565

页数：10

共 62 条

[21] NHC-Catalyzed Synthesis of ?-Sulfonyl Ketones via Radical- Mediated Sulfonyl Methylation of Aldehydes [J].

Liu, Chaolei ;

Liang, Zheng ;

Jialingbieke, Ayisenbati ;

Gao, Jian ;

Du, Ding .

ORGANIC LETTERS, 2023, 25 (15) :2657-2662

[22] Synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of α-oxocarboxylates and isocyanides [J].

Liu, Jie ;

Fan, Chao ;

Yin, Hongyu ;

Qin, Chu ;

Zhang, Guoting ;

Zhang, Xu ;

Yi, Hong ;

Lei, Aiwen .

CHEMICAL COMMUNICATIONS, 2014, 50 (17) :2145-2147

[23] Redox-Neutral Generation of Iminyl Radicals by N-Heterocyclic Carbene Catalysis: Rapid Access to Phenanthridines from Vinyl Azides [J].

Liu, Lixia ;

Zhang, Qijing ;

Wang, Chengming .

ORGANIC LETTERS, 2022, 24 (32) :5913-5917

[24] Diastereoselective Radical Aminoacylation of Olefins through N-Heterocyclic Carbene Catalysis [J].

Liu, Wen-Deng ;

Lee, Woojin ;

Shu, Hanyu ;

Xiao, Chuyu ;

Chen, Xiangyang ;

Houk, Kendall N. ;

Zhao, Jiannan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (49) :22767-22777

[25] Cobalt-catalyzed radical cyclization of isocyanides forming phenanthridine derivatives [J].

Liu, Xiangyu ;

Wu, Chengjuan ;

Zhang, Jing ;

Shi, Yihan ;

Zhang, Shengnan ;

Geng, Yan ;

Tung, Chen-Ho ;

Wang, Wenguang .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (20) :2997-3002

[26] Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes [J].

Liu, Yao ;

Li, Ji-Lin ;

Liu, Xu-Ge ;

Wu, Jia-Qiang ;

Huang, Zhi-Shu ;

Li, Qingjiang ;

Wang, Honggen .

ORGANIC LETTERS, 2021, 23 (05) :1891-1897

[27] Electrochemical initiation of electron-catalyzed phenanthridine synthesis by trifluoromethylation of isonitriles [J].

Luebbesmeyer, M. ;

Leifert, D. ;

Schaefer, H. ;

Studer, A. .

CHEMICAL COMMUNICATIONS, 2018, 54 (18) :2240-2243

[28] Metal-free radical oxidative decarboxylation/cyclization of acyl peroxides and 2-isocyanobiphenyls [J].

Pan, Changduo ;

Zhang, Honglin ;

Han, Jie ;

Cheng, Yixiang ;

Zhu, Chengjian .

CHEMICAL COMMUNICATIONS, 2015, 51 (18) :3786-3788

[29] Radical Arylalkoxycarbonylation of 2-Isocyanobiphenyl with Carbazates: Dual C-C Bond Formation toward Phenanthridine-6-carboxylates [J].

Pan, Changduo ;

Han, Jie ;

Zhang, Honglin ;

Zhu, Chengjian .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) :5374-5378

[30] Isocyanides as Acceptor Groups in MHAT Reactions with Unactivated Alkenes [J].

Puig, Jordi ;

Bonjoch, Josep ;

Bradshaw, Ben .

ORGANIC LETTERS, 2023, 25 (35) :6539-6543

← 1 2 3 4 5 6 7 →