Synthesis of 1,2-dihydro-1,3-diaza-2λ5 4λ5-2,4-diphosphorine 2-oxides

被引：13

作者：

Andújar, CM ^{[1
]}

Alvarez, IP ^{[1
]}

Ortiz, FL ^{[1
]}

机构：

[1] Univ Almeria, Almeria 04120, Spain

来源：

TETRAHEDRON | 2002年 / 58卷 / 13期

关键词：

phosphazenes; diphosphorines; carbanions; phosphorus heterocycles; SNAr;

D O I：

10.1016/S0040-4020(02)00144-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of lithium (N-diphenylphosphoryl)phosphazenes with nitriles afforded 1,2-dihydro-1,3-diaza-2lambda(5),4lambda(5)-2,4-diphosphorine 2-oxides through a C-regioselective addition to the cyano linkage followed by in situ cyclocondensation. The new heterocycles 4:1 were designed to mimic thymine and are promising chemotherapeutic anticancer agents. As an exception, for p-nitrobenzonitrile a SNAr C, reaction was exclusively observed with the nucleophile entering in the ortho position of the nitro substituent in a process directed by the strong electron withdrawing effect of the NO2 group. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2569 / 2575

页数：7

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[11] REACTION OF ALPHA-METALLATED N-ACYL-LAMBDA-5-PHOSPHAZENES WITH ARYL CYANIDES [J].

BARLUENGA, J ;

FERRERO, M ;

LOPEZ, F ;

PALACIOS, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (03) :615-618

[12]

BARLUENGA J, 1985, J CHEM RES-S, P211

[13] A FACILE AND EFFICIENT PREPARATION OF THE UNKNOWN PRIMARY BETA-ENAMINOPHOSPHINES - SYNTHESIS OF THE 1ST 1,3,4-DIAZA-LAMBDA-5-PHOSPHININES [J].

BARLUENGA, J ;

LOPEZ, F ;

PALACIOS, F .

TETRAHEDRON LETTERS, 1987, 28 (25) :2875-2878

[14] GRIGNARD-REAGENTS SELECTIVE ATTACK TO NITROARENIC FUNCTION IN THE PRESENCE OF OTHER ELECTROPHILIC GROUPS [J].

BARTOLI, G ;

BOSCO, M ;

DALPOZZO, R .

TETRAHEDRON LETTERS, 1985, 26 (01) :115-118

[15] COMPETITION BETWEEN ADDITION AND REDOX PROCESSES IN REACTIONS OF NITROARENES WITH LITHIUM-DITHIANES [J].

BARTOLI, G ;

DALPOZZO, R ;

GROSSI, L ;

TODESCO, PE .

TETRAHEDRON, 1986, 42 (09) :2563-2570

[16] FUNCTIONALIZATION OF AROMATIC SYSTEMS - A HIGHLY CHEMOSELECTIVE SYNTHESIS OF [(TRIMETHYLSILYL)METHYL]NITROARENES [J].

BARTOLI, G ;

BOSCO, M ;

DALPOZZO, R ;

TODESCO, PE .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3694-3696

[17]

BERGER S, 1993, NMR SPEKTORSKOPIE NI, V3

[18] N-PHENYL-P,P,P-TRIARYLPHOSPHA-LAMBDA-5-AZENES, TRIARYLPHOSPHINES, AND TRIARYLPHOSPHINE OXIDES - SUBSTITUENT EFFECTS ON N-15, P-13, AND C-13 NMR-SPECTRA [J].

CHOU, WN ;

POMERANTZ, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2762-2769

[19] C-13, N-15, AND P-31 NMR SPECTROSCOPIC STUDIES OF N-AROYL-P,P,P-TRIPHENYLPHOSPHA-LAMBDA-5-AZENES [J].

CHOU, WN ;

POMERANTZ, M ;

WITZCAK, MK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :716-721

[20] PHOSPHAZO COMPOUNDS FROM NITRILES .5. REACTIONS OF ACETONITRILE, PHENYLACETONITRILE AND MALONIC-ACID DINITRILE WITH [CL3=N-PCE3]CL [J].

FLUCK, E ;

SCHMID, E .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1977, 3 (02) :209-212

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