Photoinduced [3+2] Cycloaddition of Alkyl-Acceptor Diazoalkanes: Diversity-Oriented Synthesis of Pyrazolines Containing a Quaternary Center

被引:4
作者
He, Fengya [1 ]
Sun, Ziyi [1 ]
Xu, Yiwei [1 ]
Yu, Jingwen [1 ]
Li, Wenyong [2 ]
Miao, Hui [2 ]
Wu, Chenggui [1 ,2 ]
机构
[1] Anhui Univ Chinese Med, Key Lab Xinan Med, Minist Educ, Hefei 230038, Anhui, Peoples R China
[2] Fuyang Normal Univ, Sch Biol & Food Engn, Anhui Prov Key Lab Environm Hormone & Reprod, Fuyang 236037, Anhui, Peoples R China
关键词
FORMAL 4+1 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; CASCADE SYNTHESIS; DIAZO-COMPOUNDS; DIHYDROPYRAZOLES; TRANSFORMATIONS; DERIVATIVES; SELECTIVITY;
D O I
10.1021/acs.orglett.3c04296
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We present a new [3+2] cycloaddition reaction between alkyl-acceptor diazoalkanes under visible light irradiation. By employing easily accessible alkyl-acceptor-type diazoalkanes or their precursor hydrazones as both 1,3-dipoles and dipolarophiles, a diverse range of pyrazoline derivatives featuring a quaternary center have been efficiently synthesized in a predictable manner, with excellent functional group tolerance and good yields. Furthermore, scale-up experiments and downstream transformations of the product were also detailed.
引用
收藏
页码:4031 / 4036
页数:6
相关论文
共 64 条
[1]   Photochemical multicomponent transformation of acceptor-only diazoalkanes by merging their cycloaddition and carbene reactivities [J].
Cai, Bao-Gui ;
Xu, Guo-Yong ;
Xuan, Jun .
CHINESE CHEMICAL LETTERS, 2023, 34 (09)
[2]   Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate [J].
Cai Baogui ;
Xuan Jun .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (12) :4565-4574
[3]   Cinchona Alkaloid-Catalyzed Enantioselective Amination of α,β-Unsaturated Ketones: An Asymmetric Approach to Δ2-Pyrazolines [J].
Campbell, Nathaniel R. ;
Sun, Bingfeng ;
Singh, Ravi P. ;
Deng, Li .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (17) :3123-3128
[4]   Recent advances in pyrazole synthesis employing diazo compounds and synthetic analogues [J].
Chandrasekharan, Sanoop P. ;
Dhami, Anamika ;
Kumar, Sandeep ;
Mohanan, Kishor .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (45) :8787-8817
[5]   Formal [4+1] cycloaddition of in situ generated 1,2-diaza-1,3-dienes with diazo esters: facile approaches to dihydropyrazoles containing a quaternary center [J].
Chen, Bo ;
Chu, Wen-Dao ;
Liu, Quan-Zhong .
RSC ADVANCES, 2019, 9 (03) :1487-1490
[6]   Enantioselective Synthesis of Dihydropyrazoles by Formal [4+1] Cycloaddition of in Situ-Derived Azoalkenes and Sulfur Ylides [J].
Chen, Jia-Rong ;
Dong, Wan-Rong ;
Candy, Mathieu ;
Pan, Fang-Fang ;
Joerres, Manuel ;
Bolm, Carsten .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (16) :6924-6927
[7]   Use of a Traceless Activating and Directing Group for the Construction of Trifluoromethylpyrazoles: One-Pot Transformation of Nitroolefins and Trifluorodiazoethane [J].
Chen, Zhen ;
Zheng, Yan ;
Ma, Jun-An .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) :4569-4574
[8]   Recent developments in photochemical reactions of diazo compounds [J].
Ciszewski, Lukasz W. ;
Rybicka-Jasinska, Katarzyna ;
Gryko, Dorota .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (03) :432-448
[9]   Facile scalable reduction of N-acylated dihydropyrazoles [J].
Curtis, Michael D. ;
Hayes, Nancy C. ;
Matson, Patricia A. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :5035-5038
[10]   Iron catalysts with N-ligands for carbene transfer of diazo reagents [J].
Damiano, Caterina ;
Sonzini, Paolo ;
Gallo, Emma .
CHEMICAL SOCIETY REVIEWS, 2020, 49 (14) :4867-4905