A convenient synthesis of 5-(1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-diones

被引：7

作者：

Jakubiec, Dominika ^{[1
]}

Walczak, Krzysztof Z. ^{[1
]}

机构：

[1] Silesian Tech Univ, Dept Organ Chem Bioorgan Chem & Biotechnol, PL-44100 Gliwice, Poland

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 51期

关键词：

5-Cyanouracil; 1,3-Dipolar cycloaddition; Nitrite oxide; Imidoyl chloride; 5-Heteroaryluracil; ANTIVIRAL ACTIVITY; NUCLEOSIDES; ANALOGS; ISOXAZOLINE;

D O I：

10.1016/j.tetlet.2011.10.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 5-heteroaryl-substituted uracil derivatives is presented. The 1,3-dipolar cycloaddition reaction was applied for the construction of a heterocyclic ring. The nitrile oxides were obtained from the appropriate 4-substituted benzaldoximes using N-chlorosuccinimide (NCS) under basic conditions. [2+3] Cycloaddition of nitrile oxides with 5-cyanouracil as a dipolarophile gave the corresponding 5-(3-substituited-1,2,4-oxadiazol-5-yl)uracils in satisfactory yields under mild conditions. 5-Substituted uracils having an additional heterocyclic ring were obtained as a result of the [2+3] cycloaddition of 5-cyanouracil to nitrile oxides generated from thiophene-2-carbaldehyde and 5-formyluracil derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6890 / 6891

页数：2

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