An unexpected and efficient direct nucleophilic C-4 hydroxy substitution on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain

被引：11

作者：

Botta, M

Occhionero, F

Saladino, R

Crestini, C

Nicoletti, R

机构：

[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO CHIM,I-00185 ROME,ITALY

[2] UNIV VITERBO LA TUSCIA,DIPARTIMENTO AGROCHIM AGROBIOL,I-01100 VITERBO,ITALY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(97)10159-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The unexpected and efficient direct nucleophilic C-4 hydroxy (oxo) substitution by sodium alkoxides on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain is reported. An unprecedented tandem C-6 side chain Hofmann-like elimination/C-4 pyrimidinone substitution is also reported. This provides a good method for the synthesis of new C-6 vinyl cytosine derivatives. (C) 1997 Elsevier Science Ltd.

引用

页码：8249 / 8252

页数：4

共 13 条

[1] 6-ALKYL-2-METHOXY-4(3H)-PYRIMIDINONES AND 5,6-DIALKYL-2-METHOXY-4(3H)-PYRIMIDINONES IN THE TRANSFORMATIONS OF PYRIMIDINES - CONVERSION INTO 2-SUBSTITUTED "AMINO-CHLORO-PYRIMIDINE-DERIVATIVES AND 4-CHLORO-PYRIMIDINE-DERIVATIVES [J].