- Reaction of β-alkoxyvinyl α-ketoesters with acyclic NCN binucleophiles – Scalable approach to novel functionalized pyrimidines
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Two protocols for synthesis of series of low-molecular-weight di- and tri-substituted pyrimidines bearing a functional group at the 4th position, which rely on a base-mediated condensation of amidines or guanidines with β-alkoxyvinyl α-keto esters, have been developed. This approach allowed for multigram preparation of novel pyrimidine-4-carboxylates in 21–90% yield. The synthetic utility of these compounds was demonstrated by some standard functional group transformations providing promising building blocks for organic synthesis and drug discovery.
- Stepaniuk, Oleksandr O.,Rudenko, Tymofii V.,Vashchenko, Bohdan V.,Matvienko, Vitalii O.,Kondratov, Ivan S.,Tolmachev, Andrey A.,Grygorenko, Oleksandr O.
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p. 3472 - 3478
(2019/05/17)
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- New Heterospiro-ring Systems by Condensation of Some Heterocyclic o-Dicarboxylates with 1,3-Diphenylguanidine
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The behaviour of some heterocyclic o-dicarboxylates towards 1,3-diphenylguanidine and sodium hydride was investigated.Whereas the pyridine and isothiazole derivatives (11) and (22) gave the amides (12) and (13), and (23), respectively, as the main products, the pyrimidine and isoxazole esters (17) and (24) afforded, through a spiro-cyclization reaction, the heterospiro-compounds (20) and (26).The structures of these new ring systems were established on the basis of chemical and spectroscopic data.
- Nesi, Rodolfo,Chimichi, Stefano,Scotton, Mirella,Degl'Innocenti, Alessandro,Adembri, Giorgio
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p. 1667 - 1670
(2007/10/02)
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