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SYNTHESIS AND ALKYLATION OF DIETHYL 6-ARYL-2-OXO-1,2,3,6-TETRAHYDROPYRIMIDINE-4,5-DICARBOXYLATES

М. А. Колосов, М. Д. К. Ал-Огаили, В. С. Пархоменко, В. Д. Орлов
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Abstract


We have demonstrated the preparation of diethyl 6-aryl-2-oxo-1,2,3,6-tetrahydropyrimidine-4,5‑dicarboxylates by reaction of urea, oxalacetic ester, and aromatic aldehydes with substituents of various electronic properties. Alkylation of the obtained compounds in the alkyl halogenide–KOH/Н2О–MeCN system resulted in mixtures of N-alkyl derivatives, which can be separated by column chromatography. Longer reaction time led selectively to 1,3-dialkylation products.

How to Cite
Kolosov, M. A.; Al-Ogaili, M. J. K.; Parkhomenko, V. S.; Orlov, V. D. Chem. Heterocycl. Compd. 2014, 49, 1484. [Khim. Geterotsikl. Soedin. 2013, 1599.]

For this article in the English edition see DOI 10.1007/s10593-014-1399-1


Keywords


diethyl 2-oxo-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates; oxalacetic ester; alkylation; Biginelli reaction

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