Diaminomethyleneaminocarbonyldinitromethane, formed during the preparation of 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone by nitration of 2-amino-6-chloro-4(3H)-pyrimidinone

被引：7

作者：

Boyle, PH ^{[1
]}

Daly, KM ^{[1
]}

Leurquin, F ^{[1
]}

Robinson, JK ^{[1
]}

Scully, DT ^{[1
]}

机构：

[1] Univ Dublin Trinity Coll, Chem Lab, Dublin 2, Ireland

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 09期

关键词：

pyrimidines; nitration; gem-dinitro; dinitromethane; ring cleavage;

D O I：

10.1016/S0040-4039(00)02360-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Difficulties in the nitration of 2-amino-6-chloro-4(3H)-pyrimidinone to give the widely used heterocyclic precursor 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone are shown to be due to formation of an unusual open-chain gem-dinitro compound, identified as diaminomethyleneaminocarbonyldinitromethane. The latter is also formed by the nitration of 2-amino-4,6(3H,5H)-pyrimidinedione. It decomposes with loss of carbon dioxide in dimethyl sulfoxide, or in aqueous potassium hydroxide, to give guanidine and dinitromethane. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1793 / 1795

页数：3

共 11 条

[1] 6,6-DIMETHYLPTERINS - STABLE QUINOID DIHYDROPTERIN SUBSTRATE FOR DIHYDROPTERIDINE REDUCTASE AND TETRAHYDROPTERIN COFACTOR FOR PHENYLALANINE-HYDROXYLASE [J].