4-(Isoxazol-3-yl)pyrimidines from Pyrimidinyl Nitrile Oxides

被引：8

作者：

Choung, Wonken ^{[1
]}

Lorsbach, Beth A. ^{[2
]}

Sparks, Thomas C. ^{[2
]}

Ruiz, James M. ^{[2
]}

Kurth, Mark J. ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

[2] Dow AgroSci, Discovery Res, Indianapolis, IN 46268 USA

来源：

SYNLETT | 2008年 / 19期

基金：

美国国家科学基金会;

关键词：

nitrile oxide; 2-aminopyrimidine; isoxazoles; isoxazolines; ipso substitution; cycloaddition;

D O I：

10.1055/s-0028-1087346

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-dipolar cycloaddition reaction of pyrimidinyl aldoxime derived nitrile oxides and alkynes delivers 4-(isoxazol-3-yl)pyrimidines. The procedures reported accommodate three points of diversification around this bisheterocyclic scaffold and the resulting library of compounds has been added to the National Institutes of Health repository (ca. 10 mg of each with >90% purity) for pilot-scale biomedical studies with bioassay data available at the National Center for Biotechnology Information PubChem database.

引用

收藏

页码：3036 / 3040

页数：5

相关论文

共 31 条

[1] The synthesis of pyrimidin-4-yl substituted α-amino acids.: A versatile approach from alkynyl ketones [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :855-866

[2] Solid-phase synthesis of pyrido[2,3-d]pyrimidin-7-ones [J].

Angiolini, M ;

Bassini, DF ;

Gude, M ;

Menichincheri, M .

TETRAHEDRON LETTERS, 2005, 46 (50) :8749-8752

[3] The reactions of diacetylenic ketones with nitrogen nucleophiles; facile preparation of alkynyl substituted pyrimidines and pyrazoles [J].

Baldwin, JE ;

Pritchard, GJ ;

Rathmell, RE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :2906-2908

[4] Synthesis of pyrroles with fused carbocycles or heterocycles from Weinreb N-vinyl-α-amino amides [J].

Calvo, L ;

González-Ortega, A ;

Navarro, R ;

Pérez, M ;

Sañudo, MC .

SYNTHESIS-STUTTGART, 2005, (18) :3152-3158

[5] 1,3-DIPOLAR CYCLOADDITIONS .74. ORIENTATION PHENOMENA IN CYCLOADDITIONS OF ALIPHATIC AND AROMATIC NITRILE OXIDES TO ALPHA,BETA-UNSATURATED CARBOXYLIC ESTERS [J].

CHRISTL, M ;

HUISGEN, R .

CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (10) :3345-3367

[6] NEIGHBORING GROUP PARTICIPATION IN CYCLODEHYDRATION - REGIOSPECIFIC ISOXAZOLE SYNTHESIS [J].

CRAWLEY, LS ;

FANSHAWE, WJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (03) :531-532

[7] ENAMINO KETONES AS PRECURSORS OF FUNCTIONALIZED 2H-THIOPYRANS AND THIOPYRANO[2,3-C]BENZOTHIOPYRANS AND THIOPYRANO[3,2-B]BENZOTHIOPYRANS [J].

GABBUTT, CD ;

HEPWORTH, JD ;

HERON, BM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (20) :2603-2608

[8] Synthesis of new 1,5-benzodiazepines associated different 5-membered heterocycles [J].

Ghomsi, JNT ;

Ahabchane, NH ;

Essassi, EM .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (02) :353-364

[9] Carbohydrate triazoles and isoxazoles as inhibitors of galectins-1 and -3 [J].

Giguere, Denis ;

Patnam, Ramesh ;

Bellefleur, Marc-Andre ;

St-Pierre, Christian ;

Sato, Sachiko ;

Roy, Rene .

CHEMICAL COMMUNICATIONS, 2006, (22) :2379-2381

[10] Preparation of 3-(10′-halo-9′-anthracenyl) isoxazolecarboxylic esters [J].

Han, XC ;

Twamley, B ;

Natale, NR .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (03) :539-545

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