N,N'-cyclization of carbodiimides with 2-(bromomethyl)acrylic acid. A direct entry to the system 5-methylene-6H-pyrimidine-2,4-dione, a new class of thymine analogues

被引：11

作者：

Anglada, JM

Campos, T

Camps, F

Moreto, JM

Pages, L

机构：

[1] Dept. de Quim. Orgàniua Biol., C.I.D., C.S.I.C., 08034 Barcelona, Jordi Girona

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1996年 / 33卷 / 04期

关键词：

D O I：

10.1002/jhet.5570330444

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbodiimides react under very mild conditions with 2-(bromomethyl)acrylic acid at both N atoms to give 1,3-disubstituted-5-methylene-6H-pyrimidine 2,4-dione derivatives in moderate to good yields. These products behaved as good Michael accepters towards a variety of nucleophiles such as bromine, hydrochloric acid, hydrides, etc. A plausible mechanism is proposed based on theoretical approaches and experimental results.

引用

页码：1259 / 1270

页数：12

共 27 条

[1] A SI-29, C-13 AND H-1-NMR STUDY OF THE INTERACTION OF VARIOUS HALOTRIMETHYLSILANES AND TRIMETHYLSILYL TRIFLATE WITH DIMETHYL FORMAMIDE AND ACETONITRILE - A COMMENT ON THE NUCLEOPHILE INDUCED RACEMIZATION OF HALOSILANES [J].