Novel alternative for the N-S bond formation and its application to the synthesis of benzisothiazol-3-ones

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4811-4813

  Correa, Arkaitz ^a   Tellitu, Imanol ^a   Domínguez, Esther ^a   SanMartin, Raul ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750288926     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061867q     Document Type: Article

References (32)

1. For recent reviews on the synthetic applications of polyvalent iodine reagents, see: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
2. (b) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
3. (c) Wirth, T. Top. Curr. Chem. 2003, 224, 1.
4. (d) Tohma, H.; Kita, Y. Adv. Synth. Catal. 2004, 346, 111.
5. (e) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893.
6. (f) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656.
7. This ability was first reported in 1990; see: Kikugawa, Y.; Kawase, M. Chem. Lett. 1990, 581.
8. See, for example: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053.
9. (b) Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartin, R. Tetrahedron Lett. 2003, 44, 3483.
10. (c) Wardrop, D. J.; Burge, M. S. Chem. Commun. 2004, 1230.
11. (d) Correa, A.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartin, R. J. Org. Chem. 2005, 70, 2256.
12. (e) Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartin, R. Org. Lett. 2005, 7, 3073.
13. For some reviews on the chemistry of nitrenium ions, see: (a) Abramovitch, R. A.; Jeyaraman, R. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Eds.; Academic Press: Orlando, 1984; p 297.
14. (b) Falvey, D. E. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 594.
15. (c) Borodkin, G. I.; Shubin, V. G. Russ. J. Org. Chem. 2005, 41, 473.
16. Correa, A.; Tellitu, I.; Domínguez, E.; SanMartin, R. J. Org. Chem. 2006, 71, 3501. To the best of our knowledge, this is the only report in which a non-carbon species has been used as the nucleophilic counterpart of this amidation process.
17. For some selected monographs, see: (a) Pain, D. L.; Peart, B. J.; Wooldridge, K. R. H. Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon: Oxford, 1984; Vol. 6, p 175.
18. (b) Chapman, R. F.; Peart, B. J. Comprehensive Heterocyclic Chemistry II; Shinkai, I., Ed.; Pergamon: Oxford, 1996; Vol. 3, p 371.
19. Rice, W. G.; Supko, J. G.; Malspeis, L.; Buckheit, R. W.; Clanton, D.; Bu, M.; Graham, L.; Schaffer, C. A.; Turpin, J. A.; Domagala, J.; Gogliotti, R.; Bader, J. P.; Halliday, S. M.; Coren, L.; Sowder, R. C.; Arthur, L. O.; Henderson, L. E. Science 1995, 270, 1194.
20. (a) Davis, M. Adv. Heterocycl. Chem. 1972, 14, 58.
21. (b) Baggaley, K. H.; English, P. D.; Jennings, L. J. A.; Morgan, B.; Nunn, B.; Tyrrell, A. W. R. J. Med. Chem. 1985, 28, 1661.
22. Some selected examples of chlorine-free synthesis by employing (a) a PIFA-mediated Pummerer-type reaction of sulfides: Wang, H.-M.; Huang, H.-Y.; Kang, I.-J.; Chen, L.-C. Heterocycles 2001, 55, 1231.
23. (b) An amidation-cyclization process of 2,2′-dithiobenzoates: Jin, C. K.; Moon, J.-K.; Lee, W. S.; Nam, K. S. Synlett 2003, 1967.
24. (c) A transamination of sulfenamides: Shimizu, M.; Takeda, A.; Fukazawa, H.; Abe, Y.; Shibuya, I. Heterocycles 2003, 60, 1855.
25. (d) An amidation-cyclization process of 2,2′-dithiobenzamides: Sano, T.; Takagi, T.; Gama, Y.; Shibuya, I.; Shimizu, M. Synthesis 2004, 1585.
26. (a) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989.
27. (b) Novak, A.; Humphreys, L. D.; Walker, M. D.; Woodward, S. Tetrahedron Lett. 2006, 47, 5767-5769.
28. When nitrenium ions are stabilized by the electron-donating effect of a proper neighboring group (such as aryl, alkoxy, or nitrogen groups), they exhibit a sufficiently long life to undergo further organic reactions: (a) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577.
29. (b) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazama, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739.
30. (c) Falvey, D. E.; Kung, A. C. J. Org. Chem. 2005, 70, 3127.
31. Computational calculations on alkylnitrenium ions show that there is substantial hyperconjugation from the vicinal σ bonds of the N-alkyl substituent. (a) Glover, S. A.; Scott, A. P. Tetrahedron 1989, 45, 1763.
32. 3) that reacts intramolecularly with the thiole group followed by reductive elimination of iodobenzene cannot be ruled out.