Synthetic Studies on Novel 1,4-Dihydro-2-methylthio-4,4,6-trisubstituted Pyrimidine-5-carboxylic Acid Esters and Their Tautomers
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概要
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A mixture of alkyl 1,4-dihydro-2-methylthio-4,4,6-trisubstituted pyrimidine-5-carboxylate 1 and its tautomeric isomer, alkyl 1,6-dihydro-2-methylthio-4,6,6-trisubstituted pyrimidine-5-carboxylate 2 is synthesized by the Atwal–Biginelli cyclocondensation reaction of S-methylisothiourea hemisulfate salt 3 with 2-(gem-disubstituted)methylene-3-oxoesters 4 that can be accessed by the Lehnert procedure for the Knoevenagel-type condensation. The structures of the tautomeric products of the Atwal–Biginelli cyclocondensation reaction, 1 and 2, which are inseparable from each other, are determined unambiguously by 1H-NMR spectroscopy at various temperatures and nuclear Overhauser enhancement spectroscopy (NOESY) experiment. Because these dihydropyrimidine products are otherwise inaccessible and thus hitherto unavailable, the synthetic methods established in this study will help to expand the molecular diversity of their related derivatives.
著者
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OHYAMA Yoshihiko
Department of Mathematical and Life Sciences, Graduate School of Science, Hiroshima University
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Okamoto Yasuko
Faculty Of Pharmaceutical Sciences Tokushima Bunri University
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Ikunaka Masaya
Department Of Agricultural Chemistry The University Of Tokyo
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Nishimura Yoshio
Department Of Organic Chemistry Graduate School Of Pharmaceutical Sciences Tohoku University
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Ohyama Yoshihiko
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yasuda Women's University
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Nishimura Yoshio
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yasuda Women's University
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Ikunaka Masaya
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yasuda Women's University
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Nishimura Yoshio
Department of Applied Chemistry, Faculty of Engineering, Keio University
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