首页   按分类浏览 期刊浏览 卷期浏览 Ring Deformation in Spirocyclopropane‐ and Spirocyclobutane‐1′,5‐barbituric Acids
Ring Deformation in Spirocyclopropane‐ and Spirocyclobutane‐1′,5‐barbituric Acids

 

作者: Jerzy L. Mokrosz,  

 

期刊: Archiv der Pharmazie  (WILEY Available online 1986)
卷期: Volume 319, issue 12  

页码: 1141-1142

 

ISSN:0365-6233

 

年代: 1986

 

DOI:10.1002/ardp.19863191216

 

出版商: WILEY‐VCH Verlag

 

数据来源: WILEY

 

摘要:

AbstractIt is well known that the 5,5‐disubstituted barbiturates adopt the planar conformation in solution. However, kinetic investigations on the hydrolysis of spiroalkane‐1′,5‐barbiturates and the analysis of the C=O stretching vibrations showed the fivefold increase of the hydrolysis rate constants and decrease of the conjugation in the pyrimidine ring for the spirocyclobutane‐1′,5‐barbituric acid (2) in relation to those containing a cyclopentane or a cyclohexane ring. To explain these phenomena we postulated the twisting of one of the imide bonds due to the steric strain of the cyclobutane ring. Very recently we reported on our investigations on the hydrolysis of spirocyclopropane‐1′,5‐barbituric acid (1) and the13C‐NMR data of four spirobarbiturates. We concluded, that the conjugation between the cyclopropane ring and the C‐4 or C‐6 carbonyl group, possible due to the non‐planar conformation of the barbiturate ring, is responsible for the low hydrolytic reactivity of the pyrimid

 

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