Sequential 1,3-Dipolar Cycloaddition of Nitrones to β-(2-Aminophenyl) α,β-Ynones and Cyclocondensation: A New Entry to the Isoxazolino[4,5-c]quinoline Ring

被引：15

作者：

Abbiati, Giorgio ^{[2
]}

Arcadi, Antonio ^{[1
]}

Marinelli, Fabio ^{[1
]}

Rossi, Elisabetta ^{[2
]}

Verdecchia, Mirella ^{[1
]}

机构：

[1] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67100 Laquila, Italy

[2] Univ Milan, Ist Chim Organ, I-20133 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 07期

关键词：

Alkynones; Nitrones; Heterocycles; Cycloaddition; Polycycles; ORGANOBORON DERIVATIVES; ISOXAZOLINES; HETEROCYCLIZATION; REARRANGEMENT; QUINOLINES;

D O I：

10.1002/ejoc.200800994

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

The reaction of beta-(2-aminophenyl) alpha,beta-ynones with N-methyl nitrones provides a simple and efficient entry to the isoxazolino[4,5-c]quinoline ring system through a sequential 1,3-dipolar cycloaddition/anmulation process. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：1027 / 1031

页数：5

共 24 条

[1]

Abbiati G, 2003, EUR J ORG CHEM, V2003, P1423

[2]

Rh-catalyzed sequential hydroarylation/hydrovinylation-heterocyclization of β-(2-aminophenyl)-α,β-ynones with organoboron derivatives:: A new approach to functionalized quinolines [J].

Abbiati, Giorgio ;

Arcadi, Antonio ;

Marinelli, Fabio ;

Rossi, Ellsabetta ;

Verdecchia, Mirella .

SYNLETT, 2006, (19) :3218-3224

[3]

Synthesis of functionalised quinolines through tandem addition/annulation reactions of β-(2-aminophenyl)-α,β-ynones [J].

Arcadi, A ;

Marinelli, F ;

Rossi, E .

TETRAHEDRON, 1999, 55 (46) :13233-13250

[4]

Pd-catalyzed regioselective hydroarylation of α-(2-aminoaryl)-α,β-ynones with organoboron derivatives as a tool for the synthesis of quinolines:: experimental evidence and quantum-chemical calculations [J].

Arcadi, Antonio ;

Aschi, Massimiliano ;

Marinelli, Fabio ;

Verdecchia, Mirella .

TETRAHEDRON, 2008, 64 (22) :5354-5361

[5]

REACTIONS AT HIGH-PRESSURES - [3+2] DIPOLAR CYCLOADDITION OF NITRONES WITH VINYL ETHERS [J].

DICKEN, CM ;

DESHONG, P .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2047-2051

[6]

Synthesis of stable isoxazolines by [3+2] cycloaddition of oxaziridines with alkynes [J].

Fabio, Marilena ;

Ronzini, Ludovico ;

Troisi, Luigino .

TETRAHEDRON, 2008, 64 (22) :4979-4984

[7]

Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]-naphthyridines as novel topoisomerase I-targeting antitumor agents [J].

Feng, Wei ;

Satyanarayana, Mavurapu ;

Cheng, Liang ;

Liu, Angela ;

Tsai, Yuan-Chin ;

Liu, Leroy F. ;

LaVoie, Edmond J. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (20) :9295-9301

[8]

Görlitzer K, 2002, PHARMAZIE, V57, P243

[9]

Grigor'ev IA, 2008, NITRILE OXIDES, NITRONES, AND NITRONATES IN ORGANIC SYNTHESIS: NOVEL STRATEGIES IN SYNTHESIS, 2ND EDITION, P129

[10]

GRUNANGER P, 1991, CHEM HETEROCYCLIC 1, P630

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