A straightforward and efficient synthesis of 3-(pyrimidinyl)propanoates from levulinic acid

Journal of the Brazilian Chemical Society

Alex F. C. Flores²  Juliana L. Malavolta²  Alynne A. Souto²  Rayane B. Goularte²  Darlene C. Flores²  Luciana A. Piovesan¹ 

[1] ,Universidade Federal de Santa Maria Departamento de Química Núcleo de Química de HeterociclosSanta Maria RS ,Brazil

关键词: pyrimidines;    3-heteroarylpropanoates;    levulinic acid;    cyclocondensation;   

DOI  :  10.5935/0103-5053.20130070

来源: SciELO

【 摘 要 】

The cyclocondensation of methyl 7,7,7-trifluoro-4-methoxy-6-oxo-4-heptenoate and methyl 7,7,7-trichloro-4-methoxy-6-oxo-4-heptenoate, derived from levulinic acid with amidines [NH2CONH2, NH2CR(NH) (R = H, Me, Ph, NH2, SMe and 1H-pyrazol-1-yl), 5-amino-3-methyl1H-pyrazol and 2-aminothiazole] into pyrimidine and pyrimidine-like derivatives as a new type of glutamate-like 3-(trihalomethylatedpyrimidinyl)propanoate is reported. Preparation of 3-(trihalomethylatedpyrimidinyl) propanohydrazides is also described. The synthetic potential of this straightforward protocol was established by the synthesis of fourteen new 3-(pyrimidinyl) propanoates in regular to good yields (38-92%). The structural assignments were based on the analysis of their ¹H and 13C nuclear magnetic resonance (NMR) and gas chromatography-mass spectrometry (GC-MS) data.

【 授权许可】

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