Copper-Mediated Aminoazidation, Aminohalogenation, and Aminothiocyanation of β,γ-Unsaturated Hydrazones: Synthesis of Versatile Functionalized Pyrazolines

被引：40

作者：

Wang, Li-Jing ^{[1
,2
]}

Ren, Pei-Xing ^{[1
]}

Qi, Lin ^{[1
]}

Chen, Manman ^{[1
]}

Lu, Yan-Lei ^{[1
]}

Zhao, Jing-Ye ^{[1
]}

Liu, Rui ^{[1
]}

Chen, Jia-Min ^{[1
]}

Li, Wei ^{[1
,2
]}

机构：

[1] Hebei Univ, Coll Chem & Environm Sci, 180 Wusi Donglu, Baoding 071002, Peoples R China

[2] Hebei Univ, Key Lab Med Chem & Mol Diag, Minist Educ, Key Lab Chem Biol Hebei Prov, 180 Wusi Donglu, Baoding 071002, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 15期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; UNACTIVATED ALKENES; CASCADE SYNTHESIS; DIHYDROPYRAZOLES; TETRAHYDROPYRIDAZINES; DIFUNCTIONALIZATION; CYCLOADDITION; ISOXAZOLINES; SUBSTITUENT; DIAMINATION;

D O I：

10.1021/acs.orglett.8b01620

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile method for the rapid synthesis of diverse functionalized pyrazolines has been developed based on copper-mediated aminofunctionalization of beta,gamma-unsaturated hydrazones. The scope of this strategy encompasses a range of difunctionalization reactions: aminoazidation, aminohalogenation, and aminothiocyanation. These reactions provide straightforward access to a series of useful pyrazoline building blocks containing various functional groups that are hard to access traditionally.

引用

页码：4411 / 4415

页数：5

共 50 条

[1] Synthesis of acyloxyl pyrazolines by copper-mediated aminoacyloxylation of unsaturated ketohydrazones
Chen, Manman
Qi, Lin
Chen, Jia-Min
Ren, Pei-Xing
Du, Jie
Wang, Li-Jing
Li, Wei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (28) : 5136 - 5143
[2] Copper-mediated Intermolecular CC- aminohalogenation of Indoles at Room Temperature
Lu, Yuanhui
Zhang, Xiaoxiang
Xiao, Xiaoyu
Huang, Ninghua
Dou, Yadong
Liu, Chenrui
Wei, Wanxing
Zhang, Zhuan
Liang, Taoyuan
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (10)
[3] Copper-mediated reactions of a, β-unsaturated ketoximes
Morey, Tara S.
Leach, Christopher W.
Browder, Cindy C.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[4] Copper-mediated synthesis of α-trifluoromethylthio- and seleno-α,β-unsaturated carbonyl compounds
Zhu, Peitao
He, Xing
Chen, Xiaoqing
You, Yi
Yuan, Yaofeng
Weng, Zhiqiang
TETRAHEDRON, 2014, 70 (03) : 672 - 677
[5] Copper-Mediated Radical Trifluoromethylation of Unsaturated Potassium Organotrifluoroborates
Presset, Marc
Oehlrich, Daniel
Rombouts, Frederik
Molander, Gary A.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (24): : 12837 - 12843
[6] Copper-mediated synthesis of α-trifluoromethylselenolated esters
Chen, Taotao
You, Yi
Weng, Zhiqiang
JOURNAL OF FLUORINE CHEMISTRY, 2018, 216 : 43 - 46
[7] Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines
Balkenhohl, Moritz
Kolbl, Sebastian
Georgiev, Tony
Carreira, Erick M.
JACS AU, 2021, 1 (07): : 919 - 924
[8] Ambient-Light-Promoted Perfluoroalkylative Cyclization of β,γ-Unsaturated Hydrazones: Synthesis of Perfluoroalkylated Pyrazolines
Yu, Jing-miao
Cai, Chun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (40) : 6008 - 6012
[9] Copper-mediated cyclization of alpha,beta-unsaturated ketoximes
Kraft, MB
Morey, TS
Gearhart, NC
Browder, CC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U512 - U512
[10] Synthesis of Polysubstituted Furans via Copper-Mediated Annulation of Alkyl Ketones with α,β-Unsaturated Carboxylic Acids
Yang, Yuzhu
Yao, Jinzhong
Zhang, Yuhong
ORGANIC LETTERS, 2013, 15 (13) : 3206 - 3209

← 1 2 3 4 5 →