Synthesis of 4H-3,1-Benzoxazines, Quinazolin-2-ones, and Quinoline-4-ones by Palladium-Catalyzed Oxidative Carbonylation of 2-Ethynylaniline Derivatives

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2469-2477

  Costa, Mirco ^a   Della Cà, Nicola ^a   Gabriele, Bartolo ^b   Massera, Chiara ^a   Salerno, Giuseppe ^b   Soliani, Matteo ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CATALYSIS; DERIVATIVES; ISOMERS; OXIDATION; PALLADIUM; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CARBONYLATION PRODUCTS; CATALYTIC AMOUNTS;

KETONES;

ANILINE DERIVATIVE; BENZOXAZINE DERIVATIVE; CARBON MONOXIDE; PALLADIUM; POTASSIUM FLUORIDE; QUINAZOLINONE DERIVATIVE; QUINOLINE DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; ISOMERIZATION; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 1842556218     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0357770     Document Type: Article

References (49)

1. Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. J. Organomet. Chem. 2003, 687, 219-228, and references therein.
2. Gabriele, B.; Costa, M.; Salerno, G.; Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1994, 83-87.
3. Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M.; Massera, C. Eur. J. Org. Chem. 2001, 4607-4613.
4. Bacchi, A.; Costa, M.; Gabriele, B.; Pelizzi, G.; Salerno, G. J. Org. Chem. 2002, 67, 4450-4457.
5. Bacchi, A.; Chiusoli, G. P.; Costa, M.; Sani, C.; Gabriele, B.; Salerno, G. J. Organomet. Chem. 1998, 562, 35-43.
6. (a) Mura, J.-L. Eur. Pat. Appl. EP 674038, 1995.
7. (b) Phaff, R. Eur. Pat. Appl. EP 316277, 1989.
8. (c) Berneth, H. Ger. Offen. DE 3500361, 1986.
9. (d) Brack, A. Liebigs Ann. Chem. 1969, 730, 166-172.
10. (e) Brack, A. Fr. Pat. Appl. FR 1542278, 1968.
11. (a) Madhavan, G. R.; Chakrabarti, R.; Kumar, S. K. B.; Misra, P.; Mamidi, R. N. V. S.; Balraju, K.; Babu, R. K.; Suresh, J.; Lohray, B. B.; Lohrayb, V. B.; Iqbal, J.; Rajagopalan, R. Eur. J. Med. Chem. 2001, 36, 627-637.
12. (b) Parkanyi, C.; Schmidt, D. S. J. Heterocycl. Chem. 2000, 37, 725-729.
13. (c) Kowalski, P.; Mokrosz, M. J.; Majka, Z.; Kowalska, Y. J. Heterocycl. Chem. 2000, 37, 187-189.
14. (d) Abdel-Rahman, T. M. Heterocycl. Commun. 1997, 3, 535-543.
15. (e) Yamamoto, S.; Hashguchi, S.; Miki, S.; Igata, Y.; Watanabe, T.; Shiraishi, M. Chem. Pharm. Bull. 1996, 44, 734-745.
16. (f) Gilmore, J. L.; Hays, S. J.; Caprathe, B. W.; Lee, C.; Emmerling, M. R.; Michael, W.; Jean, J. C.; Bioorg. Med. Chem. Lett. 1986, 6, 679-682.
17. (g) Catarzi, D.; Cecchi, L.; Colotta, V.; Filacchioni, G.; Varano, F.; Martini, C.; Giusti, L.; Luccchini, A. J. Med. Chem. 1995, 38, 2196-2201.
18. (h) Matsumoto, Y.; Uchida, W.; Yanagisawa, I. PCT Int. Appl. WO 9418195, 1994.
19. (i) Krantz, A.; Spencer, R. W.; Tam, T. F.; Liak, T. J.; Copp, L. J.; Thomas, E. M.; Rafferty, S. P. J. Med. Chem. 1990, 33, 464-479.
20. (j) Fenton, G.; Newton, C. G.; Wyman, B. M.; Bagge, P.; Dron, D. I.; Riddell, D.; Jones, G. D. J. Med. Chem. 1989, 32, 265-272.
21. (k) Cusic, J. W.; Coyne, W. E. U. S Pat. Appl. US 3509149, 1970.
22. (a) Cassar, L. J. Organomet. Chem. 1975, 93, 253-257.
23. (b) Sonogashira, K.; Tohda, Y.; Hogihara, N. Tetrahedron Lett. 1975, 16, 4467-4470.
24. Greene, T. W.; Wuts, E. G. M. Protective Groups in Organic Synthesis, 3rd ed.; J. Wiley & Sons, Inc.: New York, 1999; pp 655-656.
25. See, for example, (a) Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914-2921.
26. (b) De Vaal, P.; Dedieu, A. J. Organomet. Chem. 1994, 478, 121-129.
27. (c) Dyker, G.; Kellner, A. Tetrahedron Lett. 1994, 35, 7633-7636.
28. (d) Gibbs, R. A.; Krishnan, U.; Dolence, J. M.; Poulter, C. D. J. Org. Chem. 1995, 60, 7821-7829.
29. (e) Li, J.; Wang, Z.; Lu, X. Organometallics 1996, 15, 2821-2828.
30. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 1999, 3305, 5-3313.
31. Oxidative mmethoxycarbonylation of ketones is a known reaction: Hamed, O.; El-Qisairi, A.; Henry, P. M. J. Org. Chem. 2001, 66, 180-185 and references therein.
32. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longmann Scientific & Technical: Essex, U.K., 1991; p 692, 1073.
33. Hill, M. L.; Raphael, R. A. Tetrahedron 1990, 46, 4587-4594.
34. (a) Xiao, W.-J.; Alper H. J. Org. Chem. 1999, 64, 9646-9652.
35. (b) Ezquerra, J.; Pedregal, C.; Lamas, C.; Barluenga, J.; Pèrez, M.; García-Martin, M. A.; Gonzáles, J. M. J. Org. Chem. 1996, 61, 5804-5812.
36. Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551-8553.
37. (a) Brunner, H.; Spetel, G. J. Organomet. Chem. 1978, 160, 149-158.
38. (b) Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longmann Scientific & Tecnical: Essex, U.K., 1991; p 708.
39. Keshavamurthy, K. S.; Vankar, Y. D.; Dhar, D. N. Synthesis 1982, 506-508.
40. (a) Yoshida, Y.; Barrett, D.; Azami, H.; Morinaga, C.; Matsumoto, S.; Matsumoto, Y.; Takasugi, H. Bioorg. Med. Chem. 1999, 7, 2647-2666.
41. (b) Hays, S. J.; Caprathe, B. W.; Gilmore, J. L.; Amin, N.; Emmerling, M. R.; Michael, W.; Nadimpalli, R.; Nath, R.; Raser, K. J.; Stafford, D.; Watson, D.; Wang, K.; Jean, J. C. J. Med. Chem. 1998, 41, 1060-1067.
42. Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1986, 27, 6397-6400.
43. Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915-3918.
44. Sakamoto, T.; Kondo, Y. Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823-1825.
45. Hassam, H. H. A. M.; Spies, H. S.; Bredenkamp, M. W. Pol. J. Chem. 2000, 74, 1589-1598.
46. Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H. Tetrahedron Lett. 1985, 26, 5963-5966.
47. Clark, A. J.; Jones, K. Tetrahedron 1992, 48, 6875-6882.
48. Kurzer, F. Organic Syntheses; Rabjohn, N., Ed.; Wiley: New York, 1963; Collect. Vol. IV, pp 49-54.
49. Izdebski, J.; Pawlak, D. Synthesis 1989, 423-425.