Synthesis of 3-substituted-3,4-dihydro-2H-1,3-benzothiazin-2-ones via a highly regioselective palladium-catalyzed carbonylation of 2-substituted-2,3- dihydro-1,2-benzisothiazoles

Journal of Organic Chemistry

Volumn 73, Issue 4, 2008, Pages 1612-1615

  Rescourio, Gwenaella ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CATALYSIS; PALLADIUM COMPOUNDS; REGIOSELECTIVITY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BENZISOTHIAZOLES;

BENZENE;

ALDEHYDE DERIVATIVE; BENZOTHIAZINE DERIVATIVE; CARBONYL DERIVATIVE; ISOTHIAZOLE DERIVATIVE; PALLADIUM;

AMINATION; ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 39349108879     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702146n     Document Type: Article

References (42)

1. (a) Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453.
2. (b) Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. Curr. Org. Chem. 2004, 8, 919.
3. (c) Vizer, S. A.; Yerzhanov, K. B.; Al Aziz Al Quntar, A.; Dembitsky, V. M. Tetrahedron 2004, 60, 5499.
4. (d) Morimoto, T.; Kakiuchi, K. Angew. Chem., Int. Ed. 2004, 43, 5580.
5. (a) El Ali, B.; Alper, H. Synlett 2000, 2, 161.
6. (b) Vasapollo, G.; Mele, G. Targets Heterocycl. Syst. 2002, 6, 197.
7. (c) Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781.
8. (a) Nagy, E.; Benedek, C.; Heil, B.; Tõrös, S. Appl. Organomet. Chem. 2002, 16, 628.
9. (b) Tõrös, S.; Gemes-Pecsi, I.; Heil, B.; Mahob, S.; Tuba, Z. J. Chem. Soc., Chem. Commun. 1992, 11, 859.
10. (a) Larksarp, C.; Alper, H. J. Org. Chem. 2000, 65, 2773.
11. (b) Larksarp, C.; Alper, H. Org. Lett. 1999, 1, 1619.
12. (c) Dhawan, R.; Dghaym, R. D.; Arndtsen, B. A. J. Am. Chem. Soc. 2003, 125, 1474.
13. (d) Boeckman, R. K., Jr.; Reed, J. E.; Ge, P. Org. Lett. 2001, 3, 3651.
14. (e) Dghaym, R. D.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2001, 40, 3228.
15. (a) Davoli, P.; Moretti, I.; Prati, F.; Alper, H. J. Org. Chem. 1999, 64, 518.
16. (b) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214.
17. (a) Van den Hoven, B. G.; El Ali, B.; Alper, H. J. Org. Chem. 2000, 65, 4131.
18. (b) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441.
19. (c) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753.
20. Wang, M.-D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20.
21. Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414.
22. (a) Soma, Y.; Yamamoto, N.; Sano, H.; Yamauchi, K.; Tamaoki, K.; Tanaka, K.; Yabushita, T. Agency of industrial Sciences and Technology. Jpn. Patent 01,299,285; Chem. Abstr. 1990, 112, 216979e.
23. (b) Souma Y. Agency of industrial Science and Technology. U.S. Patent 4,990,629.
24. (a) Dong, C.; Alper, H. Org. Lett. 2004, 6, 3489.
25. (b) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1995, 60, 8142.
26. (c) Khumtaveeporn, K.; Alper, H. J. Am. Chem. Soc. 1994, 116, 5662.
27. (d) Alper, H.; Delledone, D.; Kameyama, M.; Roberto, D. Organometallics 1990, 9, 762.
28. Szábo, J.; Varga, I.; Fodor, L.; Bernáth, G.; Sohár, P. Acta Chim. Hung. 1984, 115, 429.
29. Roberts, C. F.; Hartley, R. C. J. Org. Chem. 2004, 69, 6145.
30. Burkhard, C. A.; Schmitz, J. V.; Burnett, R. E. J. Am. Chem. Soc. 1953, 75, 5957.
31. Nicolaou, K. C.; Gray, D. L. F.; Tae, J. J. Am. Chem. Soc. 2004, 126, 613.
32. (a) Hoffmann, R. W.; Goldmann, S. Chem. Ber. 1978, 111, 2716.
33. (b) Antonjuk, D. J.; Ridley, D. D.; Smal, M. A. Aust. J. Chem. 1980, 33, 2635.
34. (c) It must be noted that the efficiency of this process is highly dependent on the nature of the alkyl amine. With some of the substrates the overall yields were acceptable (48-55%) but with some other alkyl amines, this tandem oxidation-[2,3]-sigmatropic rearrangement-nucleophilic substitution process was low yielding (see the Experimental Section). A possible solution to this problem could be to follow a different approach, see ref 15d. However, we decided to employ this strategy for all our substrates due to the inherent convenience of utilizing the "one-pot" reaction sequence,
35. (d) Kanakarajan, K.; Meier, H. Angew. Chem. 1984, 96, 220.
36. (a) Miller, E. G.; Rayner, D. R.; Thomas, H. T.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4861.
37. (b) Bickart, P.; Carson, F. W.; Jacobus, J.; Miller, E. G.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4869.
38. (c) Tang, R.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 2100.
39. (d) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147.
40. (a) Kuniyasu H.; Hiraike H.; Morita M.; Tanaka A.; Sugoh K.; Kurosawa H. J. Org. Chem. 1999, 64, 7305.
41. For some other examples on Pd-mediated carbonylation of the N-S bond, see: (b) Knapton, D. J.; Meyer, T. Y. J. Org. Chem. 2005, 70, 785.
42. (c) Kuniyasu, H.; Kato, T.; Asano, S.; Ye, J. H.; Ohmori, T.; Morita, M.; Hiraike, H.; Fujiwara, S. I.; Terao, J.; Kurosawa, H.; Kambe, N. Tetrahedron Lett., 2006, 47, 1141.