155786-92-8Relevant articles and documents
A challenging synthetic approach to phosphonium ylide-betaines of the pyrimidine series
Van Meervelt,Van Meervelt, Luc,Smolii,Smolii, Oleg B.,Mishchenko,Mishchenko, Nikolai I.,Shakhnin,Shakhnin, Dmitrii B.,Romanenko,Romanenko, Evgenii A.,Drach,Drach, Boris S.
, p. 8835 - 8852 (2007/10/03)
Adducts of the available ylide Ph3P-CHCN with acylisocyanates and their thio analogues undergo facile cyclization, promoted by hydrogen chloride in methanol, to give high yields of 2-alkyl(aryl)-4-hydroxy(mercapto)-6-oxo-1,6-dihydropyrimidin-5-yl-trip henylphosphonium chlorides suitable to prepare several types of phosphonium ylide-betaines of the pyrimidine series, the structure of which was established by chemical transformations and X-ray diffraction analysis. Despite the mesomeric character of these heterocyclic nucleophilic agents, they are alkylated in a regioselective manner, which proves this approach to be important for the synthesis of non-phosphorylated pyrimidine derivatives, which are otherwise difficult to obtain.
CYCLIZATION OF THE PRODUCTS OF THE ADDITION OF CYANOMETHYLENETRIPHENYLPHOSPHORANE TO ACYL ISOTHIOCYANATES AS A CONVENIENT ROUTE TO FUNCTIONALLY SUBSTITUTED PYRIMIDINE DERIVATIVES
Smolii, O. B.,Panchishin, S. Ya.,Drach, B. S.
, p. 1390 - 1393 (2007/10/02)
The products of the addition of a readily accessible ylide Ph3-HCN to acyl isothiocyanates undergo an easy cyclization under the action of hydrogen chloride to give 2-alkyl(aryl)-6-mercapto-4-oxo-3,4-dihydropyrimidin-5-yltriphenylphosphonium chlorid
