Base-induced Ring Cleavage of 4-Functionalized 3-Unsubstituted Isoxazoles. Synthesis of 2-Aminopyrimidines and Pyrimidine-2(3H)-thiones

1 January 1987

journal article
research article
Published by CLOCKSS Archive in HETEROCYCLES

Vol. 25 (1) , 393-397
https://doi.org/10.3987/s-1987-01-0393

Abstract

4-Functionalized 3-unsubstituted isoxazoles undergo ring cleavage when treated with bases. The resulting open chain products (.beta.-cyanoenolates, .beta.-enaminonitriles) were converted into pyrimidines, pyrimidinethiones and pyridinones by reaction with 1,3-dinucleophiles (guanidine, thiourea) and compounds having activated methylene groups.

Keywords

HETEROCYCLES

This publication has 1 reference indexed in Scilit:

Antitumor Activity and Structural Relationships of Purine Derivatives and Related Compounds against Neoplasms in Experimental Animals
Journal of Medicinal Chemistry, 1964