Regioisomers Differentiation of 5- (and 7)-Oxo-tetrahydro-7 (and 5)H-thiazolo[3,2-a]pyrimidines. NMR Spectroscopic Studies

Edwige Nicolle Groupe de Pharmacochimie Moléculaire, Laboratoire de Chimie Organique, UFR de Pharmacie - Université Joseph Fourier (Grenoble I), BP 138, 38240, Meylan-Cedex, France Phone: 76 90 26 18 Fax: 76 90 26 18

Martine Benoit-Guyod Groupe de Pharmacochimie Moléculaire, Laboratoire de Chimie Organique, UFR de Pharmacie - Université Joseph Fourier (Grenoble I), BP 138, 38240, Meylan-Cedex, France Phone: 76 90 26 18 Fax: 76 90 26 18

Claude Gey Centre de Recherches sur les Macromolécules Végétales (CERMAV)-UJF-Grenoble I

Gérard Leclerc Groupe de Pharmacochimie Moléculaire, Laboratoire de Chimie Organique, UFR de Pharmacie - Université Joseph Fourier (Grenoble I), BP 138, 38240, Meylan-Cedex, France Phone: 76 90 26 18 Fax: 76 90 26 18

Abstract

Reaction of 2-aminothiazoline with an aromatic aldehyde and diethylmalonate, in basic medium afforded two kinds of regioisomers: 5-oxo and 7-oxo-tetrahydrothioazolopyrimidines. Assignment of the structures of 5-oxo-7-phenyl-2,3,6,7-tetrahydro-5H -thiazolo[3,2-a] pyrimidine-6-ethylcarboxylate (1) and 7-oxo-5-phenyl-2,3,5,6-tetrahydro-7H -thiazolo[3,2-a] pyrimidine-6-ethylcarboxylate (2) were performed using ¹H and ¹³C NMR spectroscopy, including NOE experiments. For each regioisomer, only R∗S∗ trans-diaxial diastereoisomers were isolated and characterized.

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Regioisomers Differentiation of 5- (and 7)-Oxo-tetrahydro-7 (and 5)H-thiazolo[3,2-a]pyrimidines. NMR Spectroscopic Studies

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Regioisomers Differentiation of 5- (and 7)-Oxo-tetrahydro-7 (and 5)H-thiazolo[3,2-a]pyrimidines. NMR Spectroscopic Studies

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