Synthesis of ring-fused oxazolo- and pyrazoloisoquinolinones by a one-pot Pd-catalyzed carboxamidation and aldol-type condensation cascade process

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6181-6189

  Chouhan, Gagan ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION; CYANIDES; ESTERS; FUNCTIONAL GROUPS; PALLADIUM;

ALDOL-TYPE CONDENSATION; CASCADE PROCESS; CHEMICAL EQUATIONS; METHOXY; METHYLENE COMPOUNDS; NITROGEN-CONTAINING HETEROCYCLES; ONE POT; OXAZOLIDINONES; THREE-COMPONENT;

CONDENSATION REACTIONS;

CARBENE; ESTER; HALIDE; ISOQUINOLINE DERIVATIVE; NITRILE; NITROGEN; OXAZOLIDINONE DERIVATIVE; OXAZOLOISOQUINOLINONE; PALLADIUM; PYRAZOLIDINONE; PYRAZOLOISOQUINOLINONE; UNCLASSIFIED DRUG; ACETIC ACID DERIVATIVE; ACETONITRILE; ACETONITRILE DERIVATIVE; AMIDE; OXAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; SULFONE;

ALDOL REACTION; ARTICLE; CARBOXAMIDATION; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; METHODOLOGY; ONE POT SYNTHESIS; REACTOR CASCADE; CHEMISTRY; SYNTHESIS;

ACETATES; ACETONITRILES; AMIDES; CATALYSIS; ISOQUINOLINES; OXAZOLES; PALLADIUM; PYRAZOLES; SULFONES;

EID: 70349089014     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9010574     Document Type: Article

References (68)

1. (a) Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd ed.; Pergamon Press: New York, 2000.
2. (b) Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell: Oxford, UK, 2000.
3. (c) Katritzky, A. R.; Rees, C. W.; Scriven, E. F. Comprehensive Heterocyclic Chemistry; Elsevier Science Ltd.: Oxford, UK, 1996.
4. (d) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
5. (a) Ukita, T.; Nakamura, Y.; Kubo, A.; Yamamoto, Y.; Moritani, Y.; Saruta, K.; Higashijoma, T.; Kotera, J.; Takagi, M.; Kikkawa, K.; Omori, K. J. Med. Chem. 2001, 44, 2204.
6. (b) Rao, A. K.; Gadre, J. N.; Pendkar, S Indian J. Chem. 1997, 36, 410.
7. (c) Babjak, M.; Kanazawa, A.; Anderson, R. J.; Green, A. E. Org. Biomol. Chem. 2006, 4, 407.
8. (d) Marchand, C.; Antony, S.; Kohn, K. W.; Cushman, M.; Ioanoviciu, A.; Staker, B. L.; Burgin, A. B.; Stewart, L.; Pommier, Y. Mol. Cancer Ther. 2006, 5, 287.
9. (e) Lin, L. Z.; Cordell, G. A. Phytochemistry 1989, 28, 1295.
10. (f) Fox, B. M.; Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Staker, B. L.; Stewart, L.; Cushman, M. J. Med. Chem. 2003, 46, 3275.
11. (g) Cheng, K.; Rahier, N. J.; Eisenhauer, B. M.; Gao, R.; Thomas, S. J.; Hecht, S. M. J. Am. Chem. Soc. 2005, 127, 838.
12. (a) Kubo, K.; Ito, N.; Isomura, Y.; Sozu, I.; Homma, H.; Murakami, M. Chem. Pharm. Bull. 1979, 27, 2372.
13. (b) Mehta, G.; Shah, S. R.; Venkateswarlu, Y. Tetrahedron 1994, 50, 11729.
14. (a) Cruz, R.; Arias, M. E.; Soliveri, J. Appl. Microbiol. Biotechnol. 2000, 53, 480.
15. (b) Cruz, R.; Arias, M. S.; Arias, M. E.; Soliveri, J. J. Antibiot. 1996, 49, 700.
16. (c) Fidalgo, M. L.; Arias, M. S.; Soliveri, J.; Arias, M. E. J. Antibiot. 1992, 45, 1759.
17. (d) Fidalgo, M. L.; Alonso, J. L.; Soliveri, J.; Arias, M. E. J. Antibiot. 1992, 45, 1753.
18. (a) Coppola, G. M. J. Heterocycl. Chem. 1981, 18, 767.
19. (b) Petersen, S.; Heitzer, H. Justus Liebigs Ann. Chem. 1978, 283.
20. (a) Nicolau, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
21. (b) Dondas, H. A.; Fishwick, C. W. G.; Gai, X.; Grigg, R.; Kilner, C.; Dumronchai, N.; Kongkathip, B.; Kongkathip, N.; Ploysuk, C.; Sridharan, V. Angew. Chem., Int. Ed. 2005, 44, 7570.
22. (c) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
23. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115.
24. (e) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195.
25. (f) Grigg, R.; Inman, M.; Kilner, C.; Koppen, I.; Marchbank, J.; Selby, P. J.; Sridharan, V. Tetrahedron 2007, 63, 6152.
26. (g) Salcedo, A.; Neuville, L.; Rondot, C.; Retailleau, P.; Zhu, J. Org. Lett. 2008, 10, 857.
27. (h) Thansandote, P.; Raemy, M.; Rudolph, A.; Lautens, M. Org. Lett. 2007, 9, 5255.
28. (i) Pinto, A.; Neuville, L.; Retailleau, P.; Zhu, J. Org. Lett. 2006, 8, 4927.
29. (j) Yanada, R.; Obika, S.; Inokuma, T.; Yanada, K.; Yamashita, M.; Ohta, S.; Takemoto, Y. J. Org. Chem. 2005, 70, 6972.
30. (k) Abbiati, G.; Arcadi, A.; Canevari, V.; Capezzuto, L.; Rossi, E. J. Org. Chem. 2005, 70, 6454.
31. (l) Cuny, G.; Bois-Choussy, M.; Zhu, J. Angew. Chem., Int. Ed. 2003, 42, 4774.
32. (m) Rossi, E.; Arcadi, A.; Abbiati, G.; Attanasi, O. A.; De Crescentini, L. Angew. Chem., Int. Ed. 2002, 41, 1400.
33. (n) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
34. (a) Von Seebach, M.; Grigg, R.; De Meijere, A. Eur. J. Org. Chem. 2002, 19, 3268.
35. (b) Bedford, R. B.; Betham, M. J. Org. Chem. 2006, 71, 9403.
36. (c) Fayol, A.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 4203.
37. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Book: Sausalito, CA, 1999.
38. For palladium-catalyzed reactions in organic synthesis see: (a) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley and Sons: New York, 2002; Vol.2.
39. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; John Wiley and Sons: New York, 1995.
40. (c) Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; John Wiley and Sons: New York, 2003.
41. (d) Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: Berlin, Germany, 2005.
42. (e) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
43. (f) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: New York, 2000.
44. For palladium-catalyzed heterocycles synthesis see: (a) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum Press: NewYork, 1991.
45. (b) Minatti, A.; Muniz, K. Chem. Soc. Rev. 2007, 36, 1142.
46. (c) Takacs, E.; Varga, C.; Skoda-Foeldes, R.; Kollar, L. Tetrahedron Lett. 2007, 48, 2453.
47. (d) Karimi, F.; Langstroem, B. J. Chem. Soc., Perkin Trans. 1 2002, 2111.
48. (e) Morera, E.; Ortar, G. Tetrahedron Lett. 1998, 39, 2835.
49. (f) Mori, M.; Chiba, K.; Ohta, N.; Ban, Y. Heterocycles 1979, 13, 329.
50. (g) Perry, R. J.; Turner, S. R. J. Org. Chem. 1991, 56, 6573.
51. For recent examples of the palladium-catalyzed cascade process see: (a) Tadd, A. C.; Matsuno, A.; Fielding, M. R.; Willis, M. C. Org. Lett. 2009, 11, 583.
52. (b) Worlikar, S. A.; Larock, R. C. J. Org. Chem. 2008, 73, 7175.
53. (c) Grigg, R.; Sridharan, V.; Shah, M.; Mutton, S.; Kilner, C.; MacPherson, D.; Milner, P. J. Org. Chem. 2008, 73, 8352.
54. For palladium-catalyzed carbonylation reactions see: (a) Abbiati, G.; Arcadi, A.; Canevari, V.; Capezzuto, L.; Rossi, E. J. Org. Chem. 2005, 70, 6454.
55. (b) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042.
56. (c) Gabriele, B.; Mancuso, R.; Salerno, G.; Lupinacci, E.; Ruffolo, G.; Costa, M. J. Org. Chem. 2008, 73, 4971.
57. (d) Haddad, N.; Tan, J.; Farina, V. J. Org. Chem. 2006, 71, 5031.
58. (e) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365.
59. (f) Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2004, 69, 6772.
60. (g) Nieman, J. A.; Ennis, M. D. J. Org. Chem. 2001, 66, 2175.
61. (h) Siamaki, A. R.; Black, D. A.; Arndtsen, B. A. J. Org. Chem. 2008, 73, 1135.
62. (i) Xiao, W.-J.; Alper, H. J. Org. Chem. 1999, 64, 9646.
63. Cao, H.; McNamee, L.; Alper, H. Org. Lett. 2008, 10, 5281.
64. Vieira, T. O.; Meaney, L. A.; Shi, Y.-L.; Alper, H. Org. Lett. 2008, 10, 4899.
65. Li, Y.; Yu, Z.; Alper, H. Org. Lett. 2007, 9, 1647.
66. Chouhan, G.; Alper, H. Org. Lett. 2008, 10, 4987.
67. Yoon, N. M.; Pak, C. S.; Brown Herbert, C.; Krishnamurthy, S.; Stocky, T. P. J. Org. Chem. 1973, 38, 2786.
68. Macrind, R.; Ferguson, G.; Arsenault, G.; McAless, A. J.; Stephenson, D. K. J. Chem. Res., Synop. 1984, 360.