Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: Scope and limitations

Journal of Organic Chemistry

Volumn 75, Issue 9, 2010, Pages 3037-3046

  Paz, Jairo ^a   Pérez Balado, Carlos ^a   Iglesias, Beatriz ^a   Muñoz, Luis ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

METABOLISM; UREA;

BASIC MEDIA; CYCLIC UREAS; ELECTROPHILES; HYDROXYL GROUPS; INTRAMOLECULAR TRAPPING; SECONDARY AMINES;

CARBON DIOXIDE;

CARBAMIC ACID; CARBON DIOXIDE; CYCLIC UREA; DIAMINE DERIVATIVE; ELECTROPHILE; HYDROXYL GROUP; OXAZINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBONYLATION; CHEMICAL STRUCTURE; CROSS LINKING; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 77951841845     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100268n     Document Type: Article

References (35)

1. For selected reviews and articles, see: Kobayashi, K.; Kondo, Y. Org. Lett. 2009, 11, 2035
2. Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365
3. Arakawa, H.; Aresta, M.; Armor, J. N.; Barteau, M. A.; Beckman, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Domen, K.; DuBois, D. L.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. A.; Goodman, D. W.; Keller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer, L. E.; Marks, T. J.; Morokuma, K.; Nichoras, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Somorjai, G. A.; Stair, P. C.; Stults, B. R.; Tumas, W. Chem. Rev. 2001, 101, 953
4. Gibson, D. H. Chem. Rev. 1996, 96, 2063
5. Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747
6. McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205
7. Shi, M.; Shen, Y. M. Helv. Chim. Acta 2001, 84, 3357
8. Pérez, E. R.; da Silva, M. O.; Costa, V. C.; Rodrigues-Filho, U. P.; Franco, D. W. Tetrahedron Lett. 2002, 43, 4091
9. Chaturvedi, D.; Ray, S. Monatsh. Chem. 2006, 137, 127
10. Kodaka, M.; Tomohiro, T.; Okuno, H. J. Chem. Soc., Chem. Commun. 1993, 81
11. Kubota, Y.; Kodaka, M.; Tomohiro, T.; Okuno, H. J. Chem. Soc., Perkin Trans. 1 1993, 5
12. Casadei, M. A.; Feroci, M.; Inesi, A.; Rossi, L.; Sotgiu, G. J. Org. Chem. 2000, 65, 4759
13. Dinsmore, C. J.; Mercer, S. P. Org. Lett. 2004, 6, 2885
14. Paz, J.; Pérez-Balado, C.; Iglesias, B.; Muñoz, L. Synlett 2009, 395
15. McGhee, W.; Riley, D.; Christ, K.; Pan, Y.; Parnas, B. J. Org. Chem. 1995, 60, 2820
16. Ion, A.; Van Doorslaer, C.; Parvulescu, V.; Jacobs, P.; De Vos, D. Green Chem. 2008, 10, 111
17. Ion, A.; Parvulescu, V.; Jacobs, P.; De Vos, D. Green Chem. 2007, 9, 158
18. García-Egido, E.; Fernández-Suárez, M.; Muñoz, L. J. Org. Chem. 2008, 73, 2909
19. García-Egido, E.; Paz, J.; Iglesias, B; Muñoz, L. Org. Biomol. Chem. 2009, 7, 3991
20. Diethyl cyanophosphonate was purchased from Sigma-Aldrich as a technical grade reagent with 90% purity.
21. 3; see the Supporting Information.
22. See the Supporting Information for details.
23. Chen, L.; Wiemer, D. F. Tetrahedron Lett. 2002, 43, 2705
24. Parrott, R. W., II; Hitchcock, S. R. Tetrahedron: Asymmetry 2008, 19, 19
25. Hitchcock, S. R.; Davis, R. A.; Richmond, D. M.; Dore, D. D.; Kuschel, S. L.; Vaughn, J. F.; Wolfe, J. A.; Hamaker, C. G.; Casper, D. M.; Dingle, J. J. Heterocycl. Chem. 2008, 45, 1265
26. Parrott, R. W., II; Hamaker, C. G.; Hitchcock, S. R. J. Heterocycl. Chem. 2008, 45, 873
27. Effenberger, F.; Gutterer, B.; Jäger, J. Tetrahedron: Asymmetry 1997, 8, 459
28. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897
29. The relative and absolute configurations were established by comparison of the spectroscopic data of samples of 11a and 12a described in the literature. Claridge, T. D. W.; Davies, S. G.; Polywka, M. E. C.; Roberts, P. M.; Russell, A. J.; Savory, E. D.; Smith, A. D. Org. Lett. 2008, 23, 5433
30. Kuyl-Yeheskiely, E.; Lodder, M.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 1992, 33, 3013
31. Pilkington, M.; Wallis, J. D. J. Chem. Soc., Chem. Commun. 1993, 1857
32. Nilsson, J.; Kraszewski, A.; Stawinski, J. J. Chem. Soc., Perkin Trans. 2 2001, 2263
33. The carbamoyl azide 21 was isolated in 25% yield from the carbonylation reaction of the N -benzylated norephedrine 10f with DPPA.
34. 4.
35. Thomas, E. W.; Nishizawa, E. E.; Zimmermann, D. C.; Williams, D. J. J. Med. Chem. 1989, 32, 228