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Type of publication: research article
Type of publication (PDB): Straipsnis Clarivate Analytics Web of Science / Article in Clarivate Analytics Web of Science (S1)
Field of Science: Chemija / Chemistry (N003)
Author(s): Gefenas, Vladas;Stankevičiūtė, Živilė;Malinauskas, Albertas
Title: Novel method for the synthesis of furo[2,3-d]pyrimidines by cyclization of 4-(phenacyloxy)pyrimidine-5-carbonitriles
Is part of: Chemistry of heterocyclic compounds. , Vol. 46, iss. 3 (2010)
Extent: p. 372-374
Date: 2010
Keywords: 2-methylsulfanyl-4-(phenacyloxy)pyrimidine-5-carbonitriles - furo[2,3-d]pyrimidines;Thorpe-Ziegler cyclization;Sodium ethoxide
Abstract: It is known that alkylation of 4(3H)-pyrimidinones occurs with the formation of a mixture of N(1)-, N(3)-, and O-alkylation products [1, 2]. We have previously found [3, 4] that reaction of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone (1) with 4-substituted w-bromoacetophenones 2a,b in the presence of potassium carbonate and a catalytic amount of potassium iodide in anhydrous acetonitrile medium readily gives all three of the O-, N(1)-, and N(3)- alkylations. The main reaction course (O-alkylation) gives the 2-methylsulfanyl-4-(phenacyloxy)pyrimidine-5-carbonitriles 3a,b in preparative yields of 37-50%. In continuing our study of the alkylation of 4(3H)-pyrimidinones we report here a novel synthetic route to the furo[2,3-d]pyrimidine system via cyclization of 2-methylsulfanyl-4-(phenacyloxy)pyrimidine-5-carbonitriles 3a,b. Interest in the method of synthesis of furo[2,3-d]pyrimidines is due to the wide spectrum of biological activity of these compounds [5-8]
Affiliation(s): Chemijos institutas
Vilniaus pedagoginis universitetas
Vytauto Didžiojo universitetas
Švietimo akademija
Appears in Collections:Universiteto mokslo publikacijos / University Research Publications

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