Efficient synthesis of 2-aminothiazole-4-phenyl-5-acetamides via the open chain tautomers of γ-keto amides

Synthetic Communications

Volumn 36, Issue 4, 2006, Pages 501-507

  Tsolomiti, Georgia ^a   Tsolomitis, Athanase ^a  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

2 Aminothiazole 4 phenyl 5 acetamides; 3 benzoyl 3 bromopropionamides; 3 benzoylpropion amides

Indexed keywords

AMIDE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 31744449737     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500385001     Document Type: Article

References (18)

1. Hargrave, K. D.; Hess, F. K.; Oliver, J. T. N-(4-Substituted-thiazolyl)- oxamic acid derivatives, new series of potent, orally active antiallergy agents. J. Med. Chem. 1983, 26, 1158-1163.
2. Kane, J. L.; Hirth, B. H.; Liang, B.; Gourlie, B. B.; Nahill, S.; Barsomian, G. Ureas of 5-aminopyrazole and 2-aminothiazole inhibit growth of gram-positive bacteria. Bioorg. Med. Chem. Lett. 2003, 13, 4463-4466.
3. Bell, F. W.; Cantrell, A. S.; Högberg, M.; Jaskunas, S. R.; Johansson, N. G.; Jordan, C. L.; Kinnick, M. D.; Lind, P.; Morin, J. M., Jr.; Noréen, R. Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure -activity relationship studies of PETT analogs. J. Med. Chem. 1995, 38, 4929-4936.
4. Wiley, R. H. The preparation of thiazoles. In Organic Reactions; Wiley: New York, 1951; VI, pp. 367-409.
5. Griffin, T. S.; Woods, T. S.; Klayman, D. L. Thioureas in the synthesis of heterocycles. Adv. Heterocycl. Chem. 1975, 18, 99-158.
6. Metwally, M. A.; Abdel-Latif, E.; Amer, F. A.; Kaupp, G. Versatile 2-amino-4-substituted-1,3-thiazoles: Synthesis and reactions. J. Sulfur Chem. 2004, 25, 63-85.
7. Dondoni, A.; Marra, A. Thiazole-mediated synthetic methodology. Chem. Rev. 2004, 104, 2557-2599.
8. Dondoni, A. New perspectives in thiazole chemistry. Phosphorus, Sulfur Silicon Relat. Elem. 1985, 24, 381-418.
9. Chiron, R.; Graff, Y. γ-Ketonic acid amides. Bull. Soc. Chim. Fr. 1970, 575-583.
10. Cromwell, N. H.; Cook, K. E. γ-Oxo- and γ-hydroxy-γ- phenylbutyr-amides. Synthesis, absorption spectra, and structure studies. J. Am. Chem. Soc. 1958, 80, 4573-4577.
11. Tsolomitis, A.; Sandris, C. Some observations concerning the lactonization of 3-aroylpropionic acids. J. Heterocycl. Chem. 1983, 20, 1545-1548.
12. (a) Chiron, R.; Graff, Y. Reaction of 1,4-diacid anhydrides with meta-disubstituted aromatic compounds. III. Reaction of phenyl magnesium bromide with N-arylsuccinimides. Bull. Soc. Chim. Fr. 1967, 3715-3717;
13. (b) Laurence, C.; Chiron, R. Ultraviolet and infrared spectroscopic study of reaction products of Grignard reagents and N-substituted succinimides and condensation products of primary amines and 4-substituted 3-buten-4-olides. C. R. Acad. Sci. Paris Ser. C 1969, 268, 279-282;
14. (c) Chiron, R.; Graff, Y. γ- and δ-Oxo acid amides. Effect of chain length and of a C-substitution. Bull. Soc. Chim. Fr. 1971, 2145-2153;
15. (d) Ramachandran, R.; Chiron, R.; Graff, Y. Amides of γ- and δ-keto acids. III. Synthesis of γ-keto amides. Bull. Soc. Chim. Fr. 1972, 1031-1040.
16. β-γ-lactones. J. Chem. Soc. 1940, 438-442.
17. Hilgenkamp, R.; Zercher, C. K. Zinc carbenoid-mediated chain extension of β-keto amides. Tetrahedron 2001, 57, 8793-8800.
18. Abdulla, R. F.; Williams, J. C. An alternative route to 4-benzoyl-2-azetidinones. Tetrahedron Lett. 1980, 21, 997-1000.