New Insights on the Reaction of 2-Aminothiazole with Ethyl Bromopyruvate for the Synthesis of 6-Ethoxycarbonylimidazothiazole. Crystal Structure of 5-Acetyl-6-ethoxycarbonylimidazo[2,1-b]thiazole and 2-Ethoxycarbonyl-2-hydroxy-7-oxothiazole[2,3-b]pyrimido[2,3-d]furan

Abstract

The reaction of 2-aminothiazole 1c with ethylbromopyruvate yields two by-products 4 and 5.

References

1. E. Abignente et al., Farm. Ed. Sci., 1981, 36, 893.
2. E. Abignente, F. Arena and P. De Caprariis, Farm. Sci., 1977, 32, 735.
3. E. Abignente et al., Farm. Ed. Sci., 1984, 39, 379.
4. W. T. Bready and E. E. Hoff, J. Org. Chem., 1970, 35, 3733.
5. E. E. van Tamelen and J. W. Murphy, J. Am. Chem. Soc., 1970, 92, 7204.
6. L. Cavalca, P. Domiano and A. Musatti, Cryst. Struct. Commun. Sect. C, 1972, 1, 345; S. B. Sanni, M. De Wolf and A. T. H. Lenstra, Acta Crystallogr., Sec. C, 1984, 40, 1724; P. C. Jain, Acta Crystallogr., Sect. C., 1987, 43, 2415; G. J. S. Doad, D. I. Okor and F. Scheinmann, J. Chem. Soc., Perkin Trans. 2, 1988, 2993; G. M. Arvanitis, A. E. Griffitts, S. P. Baffic and D. M. Ho, Acta Crystallogr., Sect. C, 1996, 52, 319; V. A. Tafeenko, H. Schenk, K. A. Paseshnichenko and L. A. Aslanov, Acta Crystallogr., Sect. C, 1996, 52, 729.
7. D. Cremer and J. A. Pople, J. Am. Chem. Soc., 1975, 97, 1354.
8. W. L. Duax, C. M. Weeks and D. C. Rohrer, Top. Stereochem., 1976, 9, 271.