NHC-Catalyzed Radical Tandem Cyclization/Coupling Reaction for the Synthesis of 2-Pyrrolidinone Derivatives

被引:3
作者
Zhou, Nengneng [1 ]
Wang, Lei [1 ]
Zhao, Fangli [1 ]
Gao, Xiang [1 ]
Zhao, Xiaowei [1 ]
Zhang, Man [1 ,2 ]
机构
[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Functionalized Mol Solids, Anhui Key Lab Mol Based Mat,Minist Educ, Wuhu 241000, Anhui, Peoples R China
[2] Anhui Normal Univ, Sch Phys & Elect Informat, Wuhu 241000, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
metal-free; NHC-catalyzed; 2-pyrrolidinons; radical coupling; tandem radical cyclization; EFFICIENT SYNTHESIS; GAMMA-LACTAMS; CARBENE; AMINODIFLUOROALKYLATION; ALKENES;
D O I
10.1002/ajoc.202300334
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel strategy for synthesizing structurally diverse 2-pyrrolidinons by a NHC-catalyzed tandem radical cyclization process has been developed. This reaction proceeds through a radical coupling approach, which not only shows broad substrate scope with excellent functional group compatibility but also is quite compatible with the secondary and tertiary radicals. By using this protocol, various potentially bioactive 2-pyrrolidinons were facilely synthesized.
引用
收藏
页数:5
相关论文
共 43 条
[1]   Insulin fibrillation: toward strategies for attenuating the process [J].
Akbarian, Mohsen ;
Yousefi, Reza ;
Farjadian, Fatemeh ;
Uversky, Vladimir N. .
CHEMICAL COMMUNICATIONS, 2020, 56 (77) :11354-11373
[2]   A novel approach to chiral, nonracemic pyrrolidines by 5-exo-trig diastereoselective radical cyclization on acrylamides derived from(-)-8-aminomenthol [J].
Andrés, C ;
Duque-Soladana, JP ;
Pedrosa, R .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4282-4288
[3]   Biologically active γ-lactams: synthesis and natural sources [J].
Caruano, J. ;
Muccioli, G. G. ;
Robiette, R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (43) :10134-10156
[4]   N-heterocyclic carbene-catalyzed radical reactions [J].
Chen, Kun-Quan ;
Sheng, He ;
Liu, Qiang ;
Shao, Pan-Lin ;
Chen, Xiang-Yu .
SCIENCE CHINA-CHEMISTRY, 2021, 64 (01) :7-16
[5]   Organocatalysis by N-heterocyclic, carbenes [J].
Enders, Dieter ;
Niemeier, Oliver ;
Henseler, Alexander .
CHEMICAL REVIEWS, 2007, 107 (12) :5606-5655
[6]   Enhanced Catalytic Performance of Indenediide Palladium Pincer Complexes for Cycloisomerization: Efficient Synthesis of Alkylidene Lactams [J].
Espinosa-Jalapa, Noel Angel ;
Ke, Diandian ;
Nebra, Noel ;
Le Goanvic, Lucas ;
Mallet-Ladeira, Sonia ;
Monot, Julien ;
Martin-Vaca, Blanca ;
Bourissou, Didier .
ACS CATALYSIS, 2014, 4 (10) :3605-3611
[7]   Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes [J].
Flanigan, Darrin M. ;
Romanov-Michailidis, Fedor ;
White, Nicholas A. ;
Rovis, Tomislav .
CHEMICAL REVIEWS, 2015, 115 (17) :9307-9387
[8]   Organocatalytic Three-Component 1,2-Cyanoalkylacylation of Alkenes via Radical Relay [J].
Gao, Yu ;
Quan, Yusheng ;
Li, Zhenjiang ;
Gao, Luoyu ;
Zhang, Zhihao ;
Zou, Xin ;
Yan, Rui ;
Qu, Yuanyuan ;
Guo, Kai .
ORGANIC LETTERS, 2021, 23 (01) :183-189
[9]   Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO [J].
Guin, Joyram ;
De Sarkar, Suman ;
Grimme, Stefan ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) :8727-8730
[10]   An overview of N-heterocyclic carbenes [J].
Hopkinson, Matthew N. ;
Richter, Christian ;
Schedler, Michael ;
Glorius, Frank .
NATURE, 2014, 510 (7506) :485-496