123044-05-3Relevant academic research and scientific papers
Synthesis and Reactions of "Biginelli-Compounds". Part I
Kappe, Christian Oliver,Roschger, Peter
, p. 55 - 64 (2007/10/02)
Various reactions of 2-oxo (or thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid derivatives (Biginelli-compounds) were investigated.The site of methylation and acylation on 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester 1a and its 2-oxo derivative 9a was studied.The synthesis of pyrimidothiazines and thiazolopyrimidines was accomplished by condensation of 1a with 1,3- and 1,2-dielectrophiles.A Dimroth-like rearrangement yielding 6H-1,3-thiazines can be observed when 1a was treated with dimethylformamide and phosphorus oxychloride.The formation of indenopyrimidines can be achieved by intramolecular Friedl-Crafts acylation of 9a and 13, respectively.Finally a route for the preparation of 4,6-disubstituted-pyrimidine-5-carbonitriles is presented, starting with Biginelli-compound 25.
