Domino heck-aza-Michael reactions: A one-pot, sequential three-component approach to 1,1-dioxido-1,2-benzisothiazoline-3-acetic acid

European Journal of Organic Chemistry

Volumn , Issue 31, 2008, Pages 5254-5262

  Rolfe, Alan ^a   Young, Kyle ^a   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

Aza Michael reaction; Domino reactions; Heck reaction; Multicomponent reactions; Sultams

Indexed keywords

EID: 55049119526     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800651     Document Type: Article

References (64)

1. For reviews on domino processes, see: a) A. Padwa, S. K. Bur, Tetrahedron 2007, 63, 5341-5378;
2. b) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
3. c) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
4. d) L. F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
5. A domino reaction is defined by Tietze as a "transformation of two or more bond-forming reactions under identical reaction conditions, in which the latter transformations take place at the functionalities obtained in the former bond forming reactions." Domino Reactions in Organic Synthesis (Eds.: L. F. Tietze, G. Brasche, K. M. Gericke), Wiley-VCH, Weinheim, Germany, 2006.
6. a) S. Fustero, D. Jiménez, M. Sánchez-Roselló, C. del Pozo, J. Am. Chem. Soc. 2007, 129, 6700-6701;
7. b) H.-P. Bi, X.-Y. Liu, F.-R. Gou, L.-N. Guo, X.-H. Duan, X.-Z. Shu, Y.-M. Liang, Angew. Chem. Int. Ed. 2007, 46, 7068-7071;
8. c) X. Gai, R. Grigg, T. Khamnaen, S. Rajviroongit, V. Sridharan, L. Zhang, S. Collard, A. Keep, Tetrahedron Lett. 2003, 44, 7441-7443;
9. d) Y. Zeng, D. S. Reddy, E. Hirt, J. Aubé, Org. Lett. 2004, 6, 4993-4995;
10. e) S. Kirschbaum, H. Waldmann, Tetrahedron Lett. 1997, 38, 2829-2832.
11. a) M. Bandini, A. Eichholzer, M. Monari, F. Piccinelli, A. Umani-Romcho, Eur. J. Org. Chem. 2007, 18, 2917-2920;
12. b) D. Perdicchia, K. A. Jørgensen, J. Org. Chem. 2007, 72, 3565-3568;
13. c) G. Balme, N. Bouyssi, Metal-catalyzed cascade reactions (Ed.: T. J. J. Müller), Topics in Organometallic Chemistry, Springer Verlag, Berlin, 2006, vol. 19, pp. 115-149.
14. a) N. Barr, J. P. Bartley, P. W. Clark, P. Dyke, S. F. Dunstan, J. Organomet. Chem. 1986, 302, 117;
15. b) G. Dyker, P. Grundt, Tetrahedron Lett. 1996, 37, 619-622;
16. c) Md. W. Khan, A. F. G. M. Reza, Tetrahedron 2005, 61, 11204-11210.
17. B. K. Rao, G. H. Hamor, Pharm. Sci. 1969, 628-630.
18. a) J. Drews, Science 2000, 287, 1960-1964;
19. b) A. Scozzafava, T. Owa, A. Mastrolorenzo, C. T. Supuran, Curr. Med. Chem. 2003, 10, 925-953.
20. L. Levy, Drugs Future 1992, 17, 451-454.
21. C. Valente, R. C. Guedes, R. Moreira, J. Iley, J. Gut, P. J. Rosenthal, Bioorg. Med. Chem. Lett. 2006, 16, 4115-4119.
22. L. Zhuang, J. S. Wai, M. W. Embrey, T. E. Fisher, M. S. Egbertson, L. S. Payne, J. P. Guare Jr., J. P. Vacca, D. J. Hazuda, P. J. Felock, A. L. Wolfe, K. A. Stillmock, M. V. Witmer, G. Moyer, W. A. Schleif, L. J. Gabryelski, Y. M. Leonard, J. J. Lynch Jr., S. R. Michelson, S. D. Young, J. Med. Chem. 2003, 46, 453-456.
23. Y. Misu, H. Togo, Org. Biomol. Chem. 2003, 1, 1342-1346.
24. a) R. D. Bravo, A. A. Canepa, Synth. Commun. 2002, 32, 3675-3680;
25. b) O. O. Orazi, R. A. Corral, R. Bravo, Heteroat. Chem. 1986, 23, 1701-1708;
26. c) A. R. Katritzky, J. Wu, S. Rachwal, B. Rachwal, D. W. Macomber, T. P. Smith, Org. Prep. Proced. Int. 1992, 24, 463-467.
27. J. Lee, Y.-L. Zhong, R. A. Reamer, D. Askin, Org. Lett. 2003, 5, 4175-4177.
28. U. Chiacchio, A. Corsaro, A. Rescifina, M. Bkaithan, G. Grassi, A. Piperno, T. Privitera, T. G. Romeo, Tetrahedron 2001, 57, 3425-3433.
29. a) P. Metz, D. Seng, R. Fröhlich, Synlett 1996, 741-742;
30. b) B. Plietker, D. Seng, R. Fröhlich, P. Metz, Tetrahedron 2000, 56, 873-879;
31. c) V. O. Rogatchov, H. Bernsmann, P. Schwab, R. Fröhlich, B. Wibbeling, P. Metz, Tetrahedron Lett. 2002, 43, 4753-4756;
32. d) I. R. Greig, M. J. Tozer, P. T. Wright, Org. Lett. 2001, 3, 369-371.
33. a) M. D. McReynolds, J. M. Dougherty, P. R. Hanson, Chem. Rev. 2004, 104, 2239-2258;
34. b) J.-M. Moriggi, L. J. Brown, J. L. Castro, R. C. D. Brown, Org. Biomol. Chem. 2004, 2, 835-844;
35. c) D. Freitag, P. Schwab, P. Metz, Tetrahedron Lett. 2004, 45, 3589-3592;
36. d) S. Karsch, D. Freitag, P. Schwab, P. Metz, Synthesis 2004, 10, 1696-1712;
37. e) M. Jiménez-Hopkins, P. R. Hanson, Org. Lett. 2008, 10, 2223-2226.
38. a) S. Merten, R. Fröhlich, O. Kataeva, P. Metz, Adv. Synth. Catal. 2005, 347, 754-758;
39. b) A. Vasudevan, P. S. Tseng, S. W. Djuric, Tetrahedron Lett. 2006, 47, 8591-8593;
40. c) L. A. Paquette, R. D. Dura, N. Fosnaugh, S. Marshall, J. Org. Chem. 2006, 71, 8438-8445;
41. d) L. A. Paquette, W. R. S. Barton, J. C. Gallucci, Org. Lett. 2004, 6, 1313-1315.
42. X.-Y. Liu, C.-H. Li, C.-M. Che, Org. Lett. 2006, 8, 2707-2710.
43. a) P. Dauban, R. H. Dodd, Org. Lett. 2000, 2, 2327-2329;
44. b) P. Dauban, L. Sanière, A. Tarrade, R. H. Dodd, J. Am. Chem. Soc. 2001, 123, 7707-7708;
45. c) E. S. Sherman, S. R. Chemler, T. B. Tan, O. Gerlits, Org. Lett. 2004, 6, 1573-1575;
46. d) W. Zeng, S. R. Chemler, J. Am. Chem. Soc. 2007, 129, 12948-12949.
47. a) J.-L. Liang, S.-X. Yuan, P. W. H. Chan, C.-M. Che, Org. Lett. 2002, 4, 4507-4510;
48. b) A. Padwa, A. C. Flick, C. A. Leverett, T. Stengel, J. Org. Chem. 2004, 69, 6377-6386.
49. A. Zhou, P. R. Hanson, Org. Lett. 2008, 10, 2551-2554.
50. 3, giving the aza-Michael adduct after 2 hours.
51. a) L. Artok, H. Bulut, Tetrahedron Lett. 2004, 45, 3881-3884;
52. b) L. Botella, C. Najera, Tetrahedron Lett. 2004, 45, 1833-1836;
53. c) I. D. Gittins, F. Caruso, Angew. Chem. Int. Ed. 2001, 40, 3001-3004.
54. 2 SPE to remove Pd and organic salts.
55. 3 = OMe); experimental data for 14 is provided.
56. As previously noted in the introductory paragraph, it has been reported that this reaction does proceed but requires days and ultimately gave low yield unless the iodobenzamides were utilized instead of the aryl bromides.
57. a) N. Kanamitsu, T. Osaki, Y. Itsuji, M. Yoshimura, H. Tsujimoto, M. Soga, Chem. Pharm. Bull. 2007, 55, 1682-1688;
58. b) J. Dudash, P. Rybczynski, M. Urbanski, A. Xiang, R. Zeck, X. Zhang, Y. Zhang, U. S. Pat. Appl. Publ. 2007, p. 65;
59. c) G. Schubert, J. Rieke-Keil, J. Zapp, H.-W. Kleemann, R. Hanna, B.-G. Huang, X.-D. Wu, Y. Gourand, U. S. Pat. Appl. Publ. 2005, p. 24.
60. M. Zhang, P. Vedantham, D. L. Flynn, P. R. Hanson, J. Org. Chem. 2004, 69, 8340-8344.
61. Attempts to develop a "true" one-pot process starting from the corresponding sulfonamide were investigated. However it was discovered that lowering the equivalents of acrylic acid from 3 to 1-1.5 significantly reduced the amount of cyclic acid formed and hence the amount of corresponding amide isolated.
62. R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518-1520.
63. R. Ferraccioli, D. Carenzi, O. Rombola, M. Catellani, Org. Lett. 2004, 6, 4759-4762.
64. F. Marion, J. Coulomb, A. Servais, C. Courillon, L. Fensterbank, M. Malacria, Tetrahedron 2006, 62, 3856-3871.