Biginelli Type Reaction with Tetroses Derivatives
1988; Elsevier BV; Volume: 27; Issue: 9 Linguagem: Inglês
10.3987/com-88-4539
ISSN1881-0942
AutoresMarı́a Valpuesta, F. J. L用ez Herrera, Teresa Lupión Cobos,
Tópico(s)Synthesis and Reactions of Organic Compounds
ResumoThe reaction of 2,4-0-ethylldene-D-erythrose and -threose with methyl BCetoaoetate and urea, 0P thiourea, under the conditions of the Biglnelll type reaction, gives as principal reactron products C-polyhydroxyalkyipyrimidines derivetives.In continuation of our study on the Biginelli type reaction] '?" wlth sugar derivatives for the preparation of C-nucleosides and analogues, we wish to report a further extenslo" of our prev~ous work, with tetrose derivatives.With these compounds we tried to check the role that the presance of the free 3-OH and its different configurations of sugar.plays in the course and the results of this reaction. 4 When the 2.4-0-(1.Q)-ethylidene-D-erythrose(1 dlmeric cyclic acetal) was made to r e a c t with urea and methyl acetoacetate in conditions similar to those previously described3 , a mixture of products was yielded.By column chromatogrsphy, we have isolated the two major products, characterlred as: 4-(5R-acetoxy-2R-methyl-l.3-dioxan-4S-yl)-5-methoxycarbonyl-6-methyl-2-oxa-l.2.3,4-tetrahydropyr~d~ne( 1 (37.5%) and (4bR, 6aR, 9R, iOaS)-4.9-dimethyl-2,5-dioxo-l,2,3,4b-tetrahydra-oxan~3.2-d~-1,3-dioxanel8.7-dlpyrimidine ( 2 ) (20.2%).
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