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Synthesis 2010(15): 2583-2587  
DOI: 10.1055/s-0029-1218841
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Expedient Microwave-Assisted Synthesis of 5-Benzoylamino-2-(aralkylsulfanyl)pyrimidin-4(3H)-ones

Finn K. Hansen, Detlef Geffken*
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany
Fax: +49(40)428386573; e-Mail: geffken@chemie.uni-hamburg.de;
Further Information

Publication History

Received 18 February 2010
Publication Date:
29 June 2010 (online)

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Abstract

A rapid and efficient microwave-assisted synthesis of novel 5-benzoylamino-2-(aralkylsulfanyl)pyrimidin-4(3H)-ones by rearrangement of 4-(1-ethoxyalkylidene)-2-phenyloxazol-5(4H)-ones in the presence of S-aralkyl-substituted isothiouronium halides and triethylamine is reported

Key words

microwave-assisted synthesis - azlactones - ring expansion - rearrangement - 2-(aralkylsulfanyl)pyrimidin-4(3H)-ones

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8

CCDC 765698 contains the supplementary crystallographic data for the deposited structure. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Crystal data for compound 3a: C18H15N3O2S; Mr = 337.40; orthorhombic; Pca21; a = 17.284(5), b = 5.8034(17), c = 31.641(9) Å; V = 3173.8(16) ų; T = 100 K; Z = 8; D x = 1.412 Mg˙m-³; µ = 0.22 mm-¹; λ(Mo K α) = 0.71073 Å; F(000) = 1408; 6062 independent reflections (R int = 0.062), 4502 reflections with I > 2δ(I); refinement method, full-matrix least-squares refinement on F ²; R[F ²>2δ(F ²)] = 0.046, wR(F ²) = 0.101, S = 1.06.