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Synthesis and Cyclizations of N-(2,3-, 3,4- and 3,5-Dimethylphenyl)-β-alanines
Department of Organic Chemistry, Kaunas University of Technology, Radvilenu pl. 19, LT-50299 Kaunas, Lithuania
Institute of Biochemistry, LT-08662 Vilnius, Mokslininku 12, Lithuania
* Author to whom correspondence should be addressed.
Received: 17 February 2004; in revised form: 10 October 2004 / Accepted: 13 October 2004 / Published: 28 February 2005
Abstract: A series of 1-aryl substituted dihydro-, 5-methyldihydro- and 6-methyl-dihydro-2,4(1H,3H)pyrimidinediones and their 2-thio analogues were obtained byreaction of the corresponding β-alanines or α-methyl- and β-methyl-β-alanines with ureaor potassium thiocyanate. The reaction of N-(2,3- and 3,5-dimethylphenyl)-α-methyl-β-alanines with ethyl acetoacetate gave 1-(2,3- or 3,5-dimethylphenyl)-2,5-dimethyl-1,4,5,6-tetrahydro-4(1H)pyridones. The combined spectral data obtained by 1H-, 13C-,1 H/13C (HETCOR) NMR and IR provided useful information about the structure of theproducts synthesized in this work.
Keywords: N-Aryl-β-alanines; 1-aryl substituted dihydropyrimidinedione; dihydro- pyrimidinone-2-thione; 1; 4; 5; 6-tetrahydropyridone; NMR spectra; IR spectra
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Vaickelioniene, R.; Mickevicius, V.; Mikulskiene, G. Synthesis and Cyclizations of N-(2,3-, 3,4- and 3,5-Dimethylphenyl)-β-alanines. Molecules 2005, 10, 407-416.
Vaickelioniene R, Mickevicius V, Mikulskiene G. Synthesis and Cyclizations of N-(2,3-, 3,4- and 3,5-Dimethylphenyl)-β-alanines. Molecules. 2005; 10(2):407-416.
Vaickelioniene, Rita; Mickevicius, Vytautas; Mikulskiene, Gema. 2005. "Synthesis and Cyclizations of N-(2,3-, 3,4- and 3,5-Dimethylphenyl)-β-alanines." Molecules 10, no. 2: 407-416.