One pot synthesis of 3,5-alkylated acetophenone and methyl benzoate derivatives via an anionic domino process

Chemical Communications

Volumn , Issue 20, 2005, Pages 2633-2634

  Ballini, Roberto ^a   Barboni, Luciano ^a   Fiorini, Dennis ^a   Giarlo, Guido ^a   Palmieri, Alessandro ^a  

^a Dipartimento di Scienze Chimiche   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; ANION; BENZOIC ACID DERIVATIVE; ESTER DERIVATIVE; METHYL BENZOATE; NITROALKANE; UNCLASSIFIED DRUG;

ALKYLATION; ANIONIC DOMINO PROCESS; ARTICLE; CHEMICAL REACTION KINETICS; ONE POT SYNTHESIS; PROCESS MODEL; PROCESS OPTIMIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 20444497894     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b500846h     Document Type: Article

References (36)

1. N. Hall, Science (Washington D. C.), 1994, 266, 32-34.
2. J. Rodriguez, Synlett, 1999, 505-518.
3. (a) E. J. Corey and X.-M. Cheng, The Logic of Chemical Synthesis, John Wiley and Sons, New York, 1989;
4. (b) T. Linberg, Strategies and Tactics in Organic Synthesis, John Wiley and Sons, New York, 1989, vol. 1;
5. (c) T. L. Ho, Tactics of Organic Synthesis, Academic Press, San Diego, 1994, vol. 1;
6. (d) A. H. Haines, Methods for the Oxidation of Organic Compounds: Alkanes, Alkenes, Alkynes and Arenes, Academic Press, London, 1985, pp. 16-22 and 217-222;
7. (e) P. P. Fu and R. G. Harvey, Chem. Rev., 1978, 78, 317-361;
8. (f) K. W. Bentley and G. W. Kirby, Elucidation of Organic Structures by Physical and Chemical Methods, John Wiley and Sons, New York, 1973, pp. 1-76.
9. (a) L. Zhang, A. M. Nadzan, R. A. Heyman, D. L. Love, D. E. Mais, G. Croston, W. W. Lamph and M. F. Boehm, J. Med. Chem., 1996, 39, 2659-2663;
10. (b) B. A. Steinbaugh, H. W. Hamilton, J. V. N. Vara Prasad, K. S. Para, P. J. Tummino, D. Fergusson, E. A. Lunney and C. J. Blankley, Bioorg. Med. Chem. Lett., 1996, 6, 1099-1104;
11. (c) C. J. C. Connolly, J. M. Hamby, M. C. Schroeder, M. Barvian, G. H. Lu, R. L. Panek, A. Amar, C. Shen, A. J. Kraker, D. W. Fry, W. D. Klohs and A. M. Doherty, Bioorg. Med. Chem. Lett., 1997, 7, 2415-2420;
12. (d) X. Zhang, G. C. G. Pais, E. S. Svarovskaia, C. Marchand, A. A. Johnson, R. G. Karki, M. C. Nicklaus, V. K. Pathak, Y. Pommier and T. R. Burke, Jr, Bioorg. Med. Chem. Lett., 2003, 13, 1215-1219;
13. (e) J.-H. Li, C. F. Bigge, R. M. Williamson, S. A. Borosky, M. G. Vartanian and D. F. Ortwine, J. Med. Chem., 1995, 38, 1955-1965;
14. (f) K. Choi and A. D. Hamilton, J. Am. Chem. Soc., 2003, 125, 10241-10249;
15. (g) T. Felder and C. A. Schalley, Angew. Chem., Int. Ed., 2003, 42, 2258-2260.
16. (a) P. Bamfield and P. F. Gordon, Chem. Soc. Rev., 1984, 441-488;
17. (b) C. K. Bradsher, Chem. Rev., 1987, 87, 1277-1297.
18. R. C. Larock, Comprehensive Organic Transformations, Wiley-VCH, New York, 1st edn., 1989, ch. 5, pp. 93-103.
19. See for example: (a) P. Areces, M. V. Gil, F. J. Higes, E. Román and J. A. Serrano, Tetrahedron Lett., 1998, 39, 8557-8560;
20. (b) D. Seebach, M. S. Hoekstra and G. Protschuk, Angew. Chem., Int. Ed. Engl., 1977, 16, 321-320;
21. (c) Y. Fumoto, T. Eguchi, H. Uno and N. Ono, J. Org. Chem., 1999, 64, 6518-6521;
22. (d) K. Kostova and M. Hesse, Helv. Chim. Acta, 1995, 78, 440-446;
23. (e) R. Ballini, L. Barboni and G. Bosica, J. Org. Chem., 2000, 65, 6261-6263;
24. (f) R. Ballini, G. Bosica, D. Fiorini and G. Giarlo, Synthesis, 2001, 2003-2006;
25. (g) R. Ballini, G. Bosica, D. Fiorini and P. Righi, Synthesis, 2002, 681-685;
26. (h) R. Ballini, D. Fiorini, M. V. Gil, A. Palmieri, E. Román and J. A. Serrano, Tetrahedron Lett., 2003, 44, 2795-2797;
27. (i) R. Ballini, G. Bosica, G. Cioci, D. Fiorini and M. Petrini, Tetrahedron, 2003, 59, 3603-3608.
28. (a) R. Ballini, D. Fiorini, M. V. Gil and A. Palmieri, Tetrahedron Lett., 2003, 44, 9033-9034;
29. (b) R. Ballini and A. Rinaldi, Tetrahedron Lett., 1994, 35, 9247-9250;
30. (c) R. Ballini and G. Bosica, Tetrahedron, 1995, 51, 4213-4222;
31. (d) R. Ballini, G. Bosica, D. Fiorini, M. V. Gil and M. Petrini, Org. Lett., 2001, 3, 1265-1267.
32. Compounds of type 1 can be easily prepared in one pot by the reaction of aldehydes with an excess of nitromethane in the presence of basic alumina as a solid catalyst: R. Ballini, G. Bosica, D. Fiorini and A. Palmieri, Synthesis, 2004, 1938-1940.
33. F. T. Boyle, G. M. Davies, J. M. Wardleworth and J. C. Arnould, Imidazolyl Compounds as Inhibitors of Farnesyl-Protein Transferase, US Pat., 6 414 145 B1, 2002.
34. (a) J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508-524;
35. (b) A. Suzuki, J. Organomet. Chem., 1999, 576, 147-168;
36. (c) F. Bellina, A. Carpita and R. Rossi, Synthesis, 2004, 2419-2440.