A practical preparation of 5-(ketoaryl)thiazoles

Tetrahedron Letters

Volumn 43, Issue 49, 2002, Pages 8845-8848

  Marcantonio, Karen M ^a   Frey, Lisa F ^a   Murry, Jerry A ^a   Chen, Cheng Yi ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; KETONE DERIVATIVE; NITRILE; THIAZOLE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; HYDROLYSIS; SYNTHESIS;

EID: 0037010790     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02230-X     Document Type: Article

References (15)

1. Hantzch A., Traumann V. Ber. Dtsch. Chem. Ges. 21:1888;938.
2. For recent variations, see: (a) Lin, Y.; Seifert, C. M.; Kang, S. M.; Dusza, J. P.; Lang, S. A., Jr. J. Heterocyclic Chem. 1979, 16, 1377; (b) Knoll, A.; Liebscher, J.; Radeglia, R. J. Prakt. Chem. 1985, 3, 463; (c) Romero-Ortega, M.; Aviles, A.; Cruz, R.; Fuentes, A.; Gomez, R. M.; Plata, A. J. Org. Chem. 2000, 65, 7244; (d) Rajappa, S.; Sudarsanam, V.; Advani, B. G.; Rane, A. V. Proc. Indian Acad. Sci. 1982, 91, 445.
3. For recent variations, see: (a) Lin, Y.; Seifert, C. M.; Kang, S. M.; Dusza, J. P.; Lang, S. A., Jr. J. Heterocyclic Chem. 1979, 16, 1377; (b) Knoll, A.; Liebscher, J.; Radeglia, R. J. Prakt. Chem. 1985, 3, 463; (c) Romero-Ortega, M.; Aviles, A.; Cruz, R.; Fuentes, A.; Gomez, R. M.; Plata, A. J. Org. Chem. 2000, 65, 7244; (d) Rajappa, S.; Sudarsanam, V.; Advani, B. G.; Rane, A. V. Proc. Indian Acad. Sci. 1982, 91, 445.
4. For recent variations, see: (a) Lin, Y.; Seifert, C. M.; Kang, S. M.; Dusza, J. P.; Lang, S. A., Jr. J. Heterocyclic Chem. 1979, 16, 1377; (b) Knoll, A.; Liebscher, J.; Radeglia, R. J. Prakt. Chem. 1985, 3, 463; (c) Romero-Ortega, M.; Aviles, A.; Cruz, R.; Fuentes, A.; Gomez, R. M.; Plata, A. J. Org. Chem. 2000, 65, 7244; (d) Rajappa, S.; Sudarsanam, V.; Advani, B. G.; Rane, A. V. Proc. Indian Acad. Sci. 1982, 91, 445.
5. For recent variations, see: (a) Lin, Y.; Seifert, C. M.; Kang, S. M.; Dusza, J. P.; Lang, S. A., Jr. J. Heterocyclic Chem. 1979, 16, 1377; (b) Knoll, A.; Liebscher, J.; Radeglia, R. J. Prakt. Chem. 1985, 3, 463; (c) Romero-Ortega, M.; Aviles, A.; Cruz, R.; Fuentes, A.; Gomez, R. M.; Plata, A. J. Org. Chem. 2000, 65, 7244; (d) Rajappa, S.; Sudarsanam, V.; Advani, B. G.; Rane, A. V. Proc. Indian Acad. Sci. 1982, 91, 445.
6. Dondoni A., Fantin G., Fogagnolo M., Medici A., Pedrini P. J. Org. Chem. 53:1988;1748.
7. Sawhney I., Wilson J.R.H. J. Chem. Soc., Perkin Trans. 1. 1990;329.
8. Pyne S.G., Ung A.T. Synlett. 1998;280.
9. South M.S., Van Sant K.A. J. Heterocyclic Chem. 28:1991;1017.
10. . For precedence with thiophene, see: Graham S.L., Scholz T.H. J. Org. Chem. 56:1991;4260.
11. An excess of thiazole was used to ensure complete conversion of nitrile, though a slight excess of either substrate has been shown to effect complete reaction.
12. 13C NMR (DMSO): δ 186.4, 182.2, 152.4, 151.0, 144.4, 140.4, 122.6, 26.5, 17.0, -5.2 ppm. To remove TBS, the reaction was poured into 2N HCl and THF, aged for 1 h, and worked-up in a similar manner.
13. Analysis of reaction mixtures revealed that none of the tertiary alcohol product expected from overaddition had formed.
14. The imine stability was problematic when R=OMe, X=SMe because the HCl salt of the imine precipitated before hydrolysis was complete.
15. In some cases (entries 1-3 and 9, Table 2 ) a slow imine hydrolysis with aq. AcOH led to some cleavage of the TBS group before imine hydrolysis was complete.