[3+2]-Cycloaddition of 2H-Azirines with Nitrosoarenes: Visible-Light-Promoted Synthesis of 2,5-Dihydro-1,2,4-oxadiazoles

被引:72
作者
Cai, Bao-Gui [1 ]
Chen, Ze-Le [1 ]
Xu, Guo-Yong [3 ]
Xuan, Jun [1 ,3 ]
Xiao, Wen-Jing [2 ]
机构
[1] Anhui Univ, Coll Chem & Chem Engn, Anhui Prov Key Lab Chem Inorgan Organ Hybrid Func, Hefei 230601, Anhui, Peoples R China
[2] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China
[3] Anhui Univ, Inst Phys Sci & Informat Technol, Hefei 230601, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
SOLID-PHASE SYNTHESIS; PHOTOREDOX CATALYSIS; CYCLOADDITION; CYCLIZATION; CHEMISTRY; FUNCTIONALIZATION; DERIVATIVES; ANNULATION; 1,2,4-OXADIAZOLES; CYCLOPROPANES;
D O I
10.1021/acs.orglett.9b01416
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A formal [3 + 2]-cycloaddition reaction of 2H-azirines with nitrosoarenes has been achieved under irradiation by visible light with the assistance of organic dye photoredox catalyst. This method utilizes nitrosoarenes as efficient radical acceptors and provides a green and powerful method for a series of biologically important 1,2,4-oxadiazole derivatives in moderate to good yields.
引用
收藏
页码:4234 / 4238
页数:5
相关论文
共 50 条
[41]   Synthesis and Cytotoxicity Evaluation of Some Novel 3,5-disubstituted-1,2,4-Oxadiazoles [J].
Reddy, M. Siva Nagi ;
Kumari, B. Sailaja ;
Babu, B. Hari .
LETTERS IN DRUG DESIGN & DISCOVERY, 2012, 9 (10) :942-946
[42]   Intermolecular [3+2] Cycloaddition of Cyclopropylamines with Olefins by Visible-Light Photocatalysis [J].
Maity, Soumitra ;
Zhu, Mingzhao ;
Shinabery, Ryan Spencer ;
Zheng, Nan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) :222-226
[43]   Synthesis of 2-Aminopyrroles Via Metal-Free Annulation of Ynamides with 2H-Azirines [J].
Jiao, Lianhong ;
Wang, Yanan ;
Ding, Lixia ;
Zhang, Chaofeng ;
Wang, Xiao-Na ;
Chang, Junbiao .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (22) :15564-15570
[44]   Synthesis and reactions of highly strained 2,3-bridged 2H-azirines [J].
Banert, Klaus ;
Meier, Barbara .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :4015-4019
[45]   Visible-light-promoted synthesis of benzothiazoles from 2-aminothiophenols and aldehydes [J].
Ye, Lin-miao ;
Chen, Jie ;
Mao, Peng ;
Mao, Zhi-feng ;
Zhang, Xue-jing ;
Yan, Ming .
TETRAHEDRON LETTERS, 2017, 58 (09) :874-876
[46]   Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles [J].
Shetnev, A. A. ;
Vasilieva, E. A. ;
Proskurina, I. K. ;
Forostyanko, A. S. ;
Presnukhina, S., I ;
Tarasenko, M., V ;
Lebedev, A. S. ;
Ivanovskii, S. A. ;
Kotov, A. D. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (03) :306-314
[47]   Design, synthesis, anti-mycobacterial activity, molecular docking and ADME analysis of spiroquinoxaline-1,2,4-oxadiazoles via [3+2] cycloaddition reaction under ultrasound irradiation [J].
Kanchrana, Madhu ;
Gamidi, Rama Krishna ;
Kumari, Jyothi ;
Sriram, Dharmarajan ;
Basavoju, Srinivas .
MOLECULAR DIVERSITY, 2024, 28 (06) :3979-3991
[48]   Iron Catalyzed [3+2] Cycloaddition of Tetrahydroisoquinoline: Synthesis of Dihydropyrrolo[2,1-a]isoquinolines [J].
Liu, Si-Wei ;
Ma, Dan-Dan ;
Zhu, Xin-Xin ;
Luo, Cheng-Dan ;
Tan, Hui-Lin ;
Ju, Xiao-Li ;
Tan, Xue ;
Tang, Xiao-Hui ;
Huang, Jie ;
Wang, Jia ;
Wang, Xian-Xun ;
Cui, Hai-Lei .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (10) :1617-1622
[49]   Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles [J].
Yoshimura, Akira ;
Nguyen, Khiem C. ;
Klasen, Scott C. ;
Postnikov, Pavel S. ;
Yusubov, Mekhman S. ;
Saito, Akio ;
Nemykin, Victor N. ;
Zhdankin, Viktor V. .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (09) :1128-1133
[50]   Continuous-Flow Synthesis of 2H-Azirines and Their Diastereoselective Transformation to Aziridines [J].
Baumann, Marcus ;
Baxendale, Ian R. .
SYNLETT, 2016, 27 (01) :159-163