Domino transformation of isoxazoles to 2,4-dicarbonylpyrroles under Fe/Ni relay catalysis

被引：52

作者：

Galenko, Ekaterina E. ^{[1
]}

Galenko, Alexey V. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

机构：

[1] St Petersburg State Univ, Inst Chem, St Petersburg 198504, Russia

来源：

RSC ADVANCES | 2015年 / 5卷 / 24期

基金：

俄罗斯基础研究基金会;

关键词：

KINASE INHIBITORS; 2H-AZIRINES; PYRROLES; DISCOVERY; ACCESS;

D O I：

10.1039/c5ra01889g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The domino reaction of 5-alkoxy-or 5-aminoisoxazoles, under metal relay catalysis, with symmetric 1,3-diketones gives 4-acylpyrrole-2-carboxylic acid derivatives in high yield. Esters and amides of acyl-acetic acids react regioselectively, giving derivatives of pyrrole-2,4-dicarboxylic acid as the main products.

引用

页码：18172 / 18176

页数：5

共 48 条

[1] General and efficient indole syntheses based on catalytic amination reactions [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (03) :439-442

[2] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[3] Synthesis of mono- and bis-C-glycosylated 2,3,4-trisubstituted IH-Pyrroles as Cyclo- and acyclo-C-nucleoside analogues [J].

Alonso-Cruz, Carmen R. ;

Freire, Raimundo ;

Rodriguez, Maria S. ;

Suarez, Ernesto .

SYNLETT, 2007, (17) :2723-2727

[4] Iron dichloride induced isomerization or reductive cleavage of isoxazoles: A facile synthesis of 2-carboxy-azirines [J].

Auricchio, S ;

Bini, A ;

Pastormerlo, E ;

Truscello, AM .

TETRAHEDRON, 1997, 53 (31) :10911-10920

[5] Ambivalent role of metal chlorides in ring opening reactions of 2H-azirines: synthesis of imidazoles, pyrroles and pyrrolinones [J].

Auricchio, Sergio ;

Truscello, Ada M. ;

Lauria, Mirvana ;

Meille, Stefano V. .

TETRAHEDRON, 2012, 68 (36) :7441-7449

[6] An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals [J].

Baumann, Marcus ;

Baxendale, Ian R. ;

Ley, Steven V. ;

Nikbin, Nikzad .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :442-495

[7] Multicatalytic Synthesis of α-Pyrrolidinyl Ketones via a Tandem Palladium(II)/Indium(III)-Catalyzed Aminochlorocarbonylation/Friedel-Crafts Acylation Reaction [J].

Cernak, Tim A. ;

Lambert, Tristan H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3124-+

[8] Discovery of Pyrrole-Indoline-2-ones as Aurora Kinase Inhibitors with a Different Inhibition Profile [J].

Chiang, Chao-Cheng ;

Lin, Yu-Hsiang ;

Lin, Shu Fu ;

Lai, Chun-Liang ;

Liu, Chiawei ;

Wei, Win-Yin ;

Yang, Sheng-chuan ;

Wane, Ru-Wen ;

Teng, Li-Wei ;

Chuang, Shih-Hsien ;

Chang, Jia-Ming ;

Yuan, Ta-Tung ;

Lee, Ying-Shuen ;

Chen, Paonien ;

Chi, Wei-Kuang ;

Yang, Ju-Ying ;

Huang, Hung-Jyun ;

Liao, Chu-Bin ;

Huang, Jiann-Jyh .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (16) :5929-5941

[9] Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds [J].

Chiba, Shunsuke ;

Wang, Yi-Feng ;

Lapointe, Guillaume ;

Narasaka, Koichi .

ORGANIC LETTERS, 2008, 10 (02) :313-316

[10] The marinopyrroles [J].

Clive, Derrick L. J. ;

Cheng, Ping .

TETRAHEDRON, 2013, 69 (25) :5067-5078

← 1 2 3 4 5 →