Polymer-supported preparation of substituted phenols: A new example of simultaneous cyclization-cleavage reaction on solid phase

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8051-8054

  Katritzky, Alan R ^a   Belyakov, Sergei A ^a   Fang, Yunfeng ^a   Kiely, John S ^b  

^a University of Florida ^*  (United States)

^b Trega Biosciences Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE;

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

EID: 0032578887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01771-7     Document Type: Article

References (18)

1. 1. (a) Combinatorial Chemistry: Synthesis and Application; Wilson, S. R.; Czarnik, A. W. Eds.; John Wiley and Sons, Inc.: New York, 1997; pp. 1-269;
2. (b) Annual Reports in Combinatorial Chemistry and Molecular Diversity; Moos, W. H.; Pavia, M. R.; Ellington, A. D.; Kay, B. K. Eds.; Ecsom: Leiden, 1997; Vol. 1, pp. 1-354;
3. (c) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449;
4. (d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643.
5. 2. Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088.
6. 3. Beebe, X.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1995, 60, 4196.
7. 4. Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937.
8. 5. (a) Gowravaram, M. R.; Gallop, M. A. Tetrahedron Lett. 1997, 38, 6973;
9. (b) Whitehouse, D. L.; Nelson, K. H.; Savinov, S. N.; Austin, D. J. Tetrahedron Lett. 1997, 38, 7139.
10. 6. Hobbs De Witt, S.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad. Sci. USA 1993, 90, 6909.
11. 7. Meyers, H. V.; Dilley, G. J.; Durgin, T. L.; Powers, T. S.; Winssinger, N. A.; Zhu, H.; Pavia, M. R. Mol. Diversity, 1995, 1, 13.
12. 8. Eichinger, K.; Nussbaumer, P.; Balkan, S.; Schulz, G. Synthesis 1987, 1061.
13. 9. Katritzky, A. R.; Belyakov, S. A; Henderson, S. A.; Steel, P. J. J. Org. Chem. 1997, 62, 8215.
14. 10. Frechet, J. M. J.; de Smet, M. D.; Farrall, M. J. J. Org. Chem. 1979, 44, 1777.
15. 2, dried in vacuo. Resin 6 (24.7 g) was added to the solution of 2-bromoacetone (7) (16 g) in MeCN (200 mL) and stirred at 70-78 °C for 40 h. Work-up was similar to that described for the resin 6.
16. 12. All reaction conditions were similar in all trial runs: molar ratio chalcone 3 : polymer 8 : 1:3, reaction time: 1 h, temperature: 75 °C.
17. 4. After evaporation of the solvents, the crude product obtained was purified by column chromatography (silica, eluent - EtOAc:hexanes).
18. 2O-signal position: 70 ppm. Poor swelling of polymer 8 in chloroform and even in chloroform/DMSO mixture did not allow its characterization by NMR. Bromine content in the resin 8: 12.8%.