Synthesis of acyloxyl pyrazolines by copper-mediated aminoacyloxylation of unsaturated ketohydrazones

被引：21

作者：

Chen, Manman ^{[1
]}

Qi, Lin ^{[1
]}

Chen, Jia-Min ^{[1
]}

Ren, Pei-Xing ^{[1
]}

Du, Jie ^{[1
]}

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

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 28期

基金：

中国国家自然科学基金;

关键词：

CATALYZED DIAMINATION; UNACTIVATED ALKENES; PALLADIUM; DIFUNCTIONALIZATION; AMINOACETOXYLATION; AMINOOXYGENATION; HETEROCYCLES; ALKYNES; FUNCTIONALIZATION; CARBOAMINATION;

D O I：

10.1039/c8ob01114a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and step-economical copper-mediated intra-/intermolecular aminoacyloxylation of ,-unsaturated hydrazones has been developed. Copper carboxylates serve as both reaction promoters and carboxylate sources in these easily conducted reactions. This method provides straightforward access to diversely useful acyloxyl pyrazolines, which are hard to access traditionally, in good to excellent yields.

引用

页码：5136 / 5143

页数：8

共 61 条

[1] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].

Alexanian, EJ ;

Lee, C ;

Sorensen, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691

[2] INTRAMOLECULAR META PHOTOCYCLOADDITION OF CONFORMATIONALLY RESTRAINED 5-PHENYLPENT-1-ENES .2. STERIC AND ELECTRONIC EFFECTS CAUSED BY 4-MONOSUBSTITUTION AND 4-DISUBSTITUTION [J].

BARENTSEN, HM ;

SIEVAL, AB ;

CORNELISSE, J .

TETRAHEDRON, 1995, 51 (27) :7495-7520

[3] Recent advances in heterobimetallic palladium(II)/copper(II) catalyzed domino difunctionalization of carbon-carbon multiple bonds [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Gazzola, Silvia ;

Mazza, Alberto .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (35) :6767-6789

[4] Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2006, 62 (31) :7213-7256

[5] Catalytic Enantioselective Alkene Aminohalogenation/Cyclization Involving Atom Transfer [J].

Bovino, Michael T. ;

Chemler, Sherry R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) :3923-3927

[6] Indole, a core nucleus for potent inhibitors of tubulin polymerization [J].

Brancale, Andrea ;

Silvestri, Romano .

MEDICINAL RESEARCH REVIEWS, 2007, 27 (02) :209-238

[7] Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters [J].

Casavant, Barbara J. ;

Khoder, Zainab M. ;

Berhane, Ilyas A. ;

Chemler, Sherry R. .

ORGANIC LETTERS, 2015, 17 (24) :5958-5961

[8] Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenes [J].

Chemler, Sherry R. ;

Fuller, Peter H. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1153-1160

[9] v Catalytic Aminohalogenation of Alkenes and Alkynes [J].

Chemler, Sherry R. ;

Bovino, Michael T. .

ACS CATALYSIS, 2013, 3 (06) :1076-1091

[10] Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes [J].

Chen, Chaohuang ;

Chen, Pinhong ;

Liu, Guosheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) :15648-15651

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