Phenyliodine(III) Bis(trifluoroacetate) Mediated Synthesis of 6-Piperidinylpurine Homo-N-nucleosides Modified with Isoxazolines or Isoxazoles

被引：10

作者：

Balalas, Thomas ^{[1
]}

Peperidou, Catherine ^{[2
]}

Hadjipavlou-Litina, Dimitra J. ^{[2
]}

Litinas, Konstantinos E. ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Greece

[2] Aristotle Univ Thessaloniki, Sch Pharm, Dept Pharmaceut Chem, Thessaloniki 54124, Greece

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 02期

关键词：

modified homo-N-nucleosides; isoxazolines; isoxazoles; 1; 3-dipolar cycloaddition reactions; phenyliodine(III) bis(trifluoroacetate); PIFA; NITRILE OXIDES; CARBOCYCLIC NUCLEOSIDES; PURINE; RING; GENERATION; ALDOXIMES; DISCOVERY; ADENOSINE; ANALOGS; OXIMES;

D O I：

10.1055/s-0035-1560704

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The room temperature, 1,3-dipolar cycloaddition reactions of the nitrile oxide obtained from (6-piperidin-1-yl-9H-purin-9-yl)acetaldehyde oxime upon phenyliodine(III) bis(trifluoroacetate) treatment with excess unsaturated alcohols as solvent resulted in isoxazoline or isoxazole derivatives in almost quantitative yields. Analogous derivatives were prepared from the reactions of unsaturated phosphates. Preliminary biological tests indicated inhibition of lipid peroxidation for some of the examined compounds.

引用

页码：281 / 292

页数：12

共 63 条

[1]

[Anonymous], 2014, 2 PHARM SCI C OCT 9, P13

[2] Synthesis of novel carbocyclic nucleosides with a cyclopentenyl ring:: Homocarbovir and analogues [J].

Balo, C ;

Blanco, JM ;

Fernández, F ;

Lens, E ;

López, C .

TETRAHEDRON, 1998, 54 (12) :2833-2842

[3]

Belen'kii LI, 2008, NITRILE OXIDES, NITRONES, AND NITRONATES IN ORGANIC SYNTHESIS: NOVEL STRATEGIES IN SYNTHESIS, 2ND EDITION, P1

[4]

Blanco JM, 2003, CHEM PHARM BULL, V51, P1060

[5] A mild and chemoselective method for the reduction of conjugated isoxazolines to β-hydroxy ketones [J].

Bode, JW ;

Carreira, EM .

ORGANIC LETTERS, 2001, 3 (10) :1587-1590

[6] FORMATION OF 1,3-DIENETRICARBONYLIRON COMPLEXES FROM THE REACTION OF DIPOTASSIUM TETRACARBONYLFERRATE WITH ALLYLIC COMPOUNDS [J].

BUTSUGAN, Y ;

YAMASHITA, A ;

ARAKI, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 287 (01) :103-108

[7] Generation of nitrile oxides under nanometer micelles built in neutral aqueous media: Synthesis of novel glycal-based chiral synthons and optically pure 2,8-dioxabicyclo[4.4.0]decene core [J].

Chatterjee, Nirbhik ;

Pandit, Palash ;

Halder, Samiran ;

Patra, Amarendra ;

Maiti, Dilip K. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7775-7778

[8] Diastereoselective synthesis of homo-N,O-nucleosides [J].

Chiacchio, U ;

Genovese, F ;

Iannazzo, D ;

Librando, V ;

Merino, P ;

Rescifina, A ;

Romeo, R ;

Procopio, A ;

Romeo, G .

TETRAHEDRON, 2004, 60 (02) :441-448

[9] Cycloaddition Methodology: A Useful Entry Towards Biologically Active Heterocycles [J].

Chiacchio, Ugo ;

Padwa, Albert ;

Romeo, Giovanni .

CURRENT ORGANIC CHEMISTRY, 2009, 13 (05) :422-447

[10]

Concalves E. S. B, 2013, BEILSTEIN J ORG CHEM, V9, P2387

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