An unprecedented Pd-catalyzed, water-promoted sequential oxidative aminocarbonylation-cyclocarbonylation process leading to 2-oxazolidinones

Organic Letters

Volumn 9, Issue 17, 2007, Pages 3319-3322

  Gabriele, Bartolo ^a   Plastina, Pierluigi ^a   Salerno, Giuseppe ^a   Mancuso, Raffaella ^a   Costa, Mirco ^b  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE; PALLADIUM; WATER;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; OXAZOLIDINONES; OXIDATION-REDUCTION; PALLADIUM; WATER;

EID: 34548190050     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071332c     Document Type: Article

References (32)

1. For reviews, see: (a) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 2005, 61, 8073-8094.
2. (b) Vicario, J. L.; Badia, D.; Carrillo, L.; Reyes, E.; Etxebarria, J. Curr. Org. Chem. 2005, 9, 219-235.
3. (c) Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichim. Acta 1997, 30, 3-12.
4. (d) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
5. (e) Evans, D. A. Aldrichim. Acta 1982, 15, 23-32.
6. For reviews, see: (a) Mukhtar, T. A.; Wright, G. D. Chem. Rev. 2005, 105, 529-542.
7. (b) Hutchinson, D. K. Expert Opin. Ther. Pat. 2004, 14, 1309-1328.
8. (b) Bozdogan, M.; Appelbaum, P. C. Int. J. Antimicrob. Ag. 2004, 23, 113-119.
9. (c) Colizza, S.; Rossi, S.; Rodio, F.; Carnuccio, P.; Cucchiara G. J. Chemother. 2003, 323-328.
10. (d) Johnson, A. P. Idrugs 2003, 6, 240-245.
11. (e) Barbachyn, M. R.; Ford, C. W. Angew. Chem., Int. Ed. 2003, 42, 2010-2023.
12. (f) Hutchinson, D. K. Curr. Top. Med. Chem. 2003, 3, 1021-1042.
13. (g) Moellering, R. C. Ann. Intern. Med. 2003, 138, 135-142.
14. (h) Diekema, D. J.; Jones, R. N. Drugs 2000, 59, 7-16.
15. (i) Müller, M.; Schimz, K. L. Cell. Mol. Life Sci. 1999, 56, 280-285.
16. (j) Brickner, S. J. Curr. Pharm. Design 1996, 2, 175-194.
17. For a review on synthetic methods for the construction of the 2-oxazolidinone ring, see: Zappia, G.; Gacs-Baitz, E.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Curr. Org. Synth. 2007, 4, 81-135.
18. We have recently reported the synthesis of 4,4-dialkyl-5-[(methoxy- carbonyl)methylene]oxazolidin-2-ones by Pd-catalyzed sequential oxidative carboxylation-methoxycarbonylation of α,α-dialkyl substituted 2-ynyl-amines: (a) Bacchi, A.; Chiusoli, G. P.; Costa, M.; Gabriele, B.; Righi, C.; Salerno, G. Chem. Commun. 1997, 1209-1210.
19. (b) Chiusoli, G. P.; Costa, M.; Gabriele, B.; Salerno, G. J. Mol. Catal. A: Chem. 1999, 143, 297-310. In that reaction, carbon dioxide was incorporated into the cycle, while carbon monoxide was incorporated into the (methoxycarbony1)methylene moiety, so the process was completely different from that described in the present work, in which both the carbonyl groups present in the final product derive from carbon monoxide. The direct formation of 5-methylene-2-oxazolidinones by carboxylation of 2-ynylamines has also been reported; see, for example:
20. (c) Costa, M.; Chiusoli, G. P.; Taffurelli, D.; Dalmonego, G. J. Chem. Soc., Perkin Trans. 1 1998, 1541-1546.
21. (d) Maggi, R.; Bertolotti, C.; Orlandini, E.; Oro, C.; Sartori, G.; Selva, M. Tetrahedron Lett. 2007, 48, 2131-2134.
22. For recent reviews on sequential catalysis, see: (a) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001-1020.
23. (b) Lee, J. M.; Na, J.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302-312.
24. (c) Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365-2379. See also:
25. 2, see:
26. (e) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. Adv. Synth. Catal. 2006, 348, 1101-1109.
27. (f) Gabriele, B.; Mancuso, R.; Salerno, G.; Veltri, L. Chem. Commun. 2005, 271-273.
28. -2 mmol), KI (70.0 mg, 0.42 mmol), and a solution of 1 (4.2 mmol) and the amine 2 (21.0 mmol) in DME (8.4 mL). Water (380 mL, 21.1 mmol) was then added, and the autoclave was sealed. While the mixture was stirred, the autoclave was charged with CO (16 atm) and air (up to 20 atm), and then heated at 100 °C with stirring for the required time. After cooling, the autoclave was degassed and opened. The solvent was evaporated, and the products were purified by column chromatography on neutral alumina using suitable hexane-AcOEt mixtures as eluent (see the Supporting Information for further details).
29. Primary amines afforded the corresponding symmetrical ureas, according to a reactivity that we have already reported: Gabriele, B.; Salerno, G.; Mancuso, R.; Costa, M. J. Org. Chem. 2004, 69, 4741-4750.
30. Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M. J. Organomet. Chem. 2001, 622, 84-88.
31. Gabriele, B., Costa, M.; Salerno, G.: Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1994, 83-87.
32. The reaction of simple, unsubstituted benzylprop-2-ynylamine led to a complex mixture of unidentified, chromatographically immobile materials.