An efficient synthesis of phenanthro-fused thiazoles by a non-phenolic oxidative coupling procedure of 4,5-diarylthiazoles

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5067-5070

  Moreno, I ^a   Tellitu, I ^a   SanMartin R ^a   Badia D ^a   Carrillo, L ^a   Dominguez E ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PHENANTHRENE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033516628     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00982-X     Document Type: Article

References (26)

1. a) Olivera, R.; Pascual, S.; Herrero, M.; SanMartín, R.; Domínguez, E. Tetrahedron Lett. 1998, 39, 7155-7158.
2. b) Domínguez, E.; Ibeas, E.; Martínez de Marigorta, E.; Palacios, J. K.; SanMartín, R. J. Org. Chem. 1996, 61, 5435-5439.
3. a) Chen, K-X.; Gresh, N.; Pulman, B. Nucleic Acid Research 1986, 14, 9103-9115.
4. b) Kumar, S. J. Org. Chem. 1997, 62, 8535-8539.
5. a) Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435-7438.
6. b) Michael, J. P. Nat. Prod. Rep. 1994, 11, 639-657.
7. c) Govindachari, T. R.; Viswanathan, N.; Radhakrishnan, J.; Pai, B. R.; Natarajan, S.; Subramaniam, P. S. Tetrahedron 1973, 29, 891-897.
8. d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans 1 1982, 2477-2485.
9. a) Nicolau, K. C.; Finlay, M. R. V.; Ninkovic, S.; Sarabia, F. Tetrahedron 1998, 54, 7127-7166.
10. b) Andrus, M. B.; Li, W.; Keyes, R. F. Tetrahedron Lett. 1998, 39, 5465-5468.
11. c) Foster, M. P.; Concepción, G. P.; Caraan, G. B.; Ireland, C. M. J. Org. Chem. 1992, 57, 6671-6675.
12. d) Abe, H.; Kushida, K.; Shiobara, Y.; Kodama, M. Tetrahedron Lett. 1988, 29, 1401-1404.
13. Suzuki, Y.; Ojika, M.; Shakagami, Y.; Fudou, R.; Yamanaka, S. Tetrahedron 1998, 54, 11399- 11404.
14. Röster, A.; Boldt, P. Synthesis 1998, 980-982.
15. Wipf, P.; Fritch, P. C.; Geib, S. J.; Sefler, A. M. J. Am. Chem. Soc. 1998, 120, 4105-4112.
16. 1,2-aminoethanethiol is the simplest commercially available aminothiol.
17. Domínguez, E.; Martínez de Marigorta, E.; SanMartín, R.; Olivera, R. Synlett 1995, 955-956 and references cited therein.
18. Landais, Y.; Robin, J-P. Tetrahedron 1992, 48, 7185-7198.
19. a) Bodin, N.; Bushby, R. J.; Cammidge, A. N.; Headdock, G. Synthesis 1995, 31-32.
20. b) Herbert, R. B.; Kattah, A. E.; Murtagh, A. J.; Sheldrake, P. W. Tetrahedron Lett. 1995, 36, 5649-5650.
21. a) see ref. 3a.
22. b) Halton, B.; Maidment, A. I.; Officer, D. L.; Warnes, J. M. Aust. J. Chem. 1984, 37, 2119-2128.
23. Kita, Y.; Gyoten, M.; Ohtsubo, M.; Tohma, H.; Takada, T. Chem. Commun. 1996, 1481-1482.
24. Following the general procedure outlined in the text, 4,5-diarylthiazoles 5c, 5d, 5e and 5f were regioselectively prepared from 4c, 4d, 4e and 4f in excellent yields: 91%, 94%, 89% and 92% respectively. In each case the assigned regiochemistry was based on previous reports. See for example: Ramana, M. M. V.; Dubhashi, D. S.; D'Souza, J. J. J. Chem. Research (S) 1998, 496-496 and references cited therein.
25. Compound 6g was detected, but not isolated, by MS. The actual structure (a priori two regioisomers can be formed) could not be established. Precursor 5g had to be prepared by an alternative route (shown below) since the Friedel-Crafts acylation approach has severe limitations: i) highly activated rings are needed on one of the aromatic rings; ii) mixture of isomers can be obtained; iii) the availability of commercial precursors (arylacetic acids or arylacetyl halides) is small. Synthetic and experimental details of these two complementary syntheses will be published elsewhere. (Formula Presented)
26. All new compounds gave satisfactory spectroscopic data.