One-pot synthesis of substituted isothiazol-3(2H)-ones: Intramolecular annulation of α-carbamoyl ketene-S,S-acetals via PIFA-mediated N-S bond formation

Synthesis

Volumn , Issue 18, 2007, Pages 2791-2796

  Huang, Jie ^a   Lu, Yumei ^a   Qiu, Baofu ^a   Liang, Yongjiu ^a   Li, Nan ^a   Dong, Dewen ^a,b  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

Author keywords

carbamoyl ketene S,S acetals; Amidation; Cyclization; Hypervalent iodine reagent; Isothiazol 3(2H) ones; Trifluoroacetic acid

Indexed keywords

HYPERVALENT IODINE REAGENT; INTRAMOLECULAR AMIDATION; ISOTHIAZOL-3(2H)-ONES; TRIFLUOROACETIC ACID;

ACETAL RESINS; ACETIC ACID; AMIDES; CYCLIZATION; IODINE; SYNTHESIS (CHEMICAL);

KETONES;

ACETAL DERIVATIVE; ALPHA CARBAMOYL KETENE S,S ACETAL DERIVATIVE; IODINE; ISOTHIAZOLE 3(2H) ONE DERIVATIVE; ISOTHIAZOLE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

AMIDATION; ANNULATION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ONE POT SYNTHESIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34948838314     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983875     Document Type: Article

References (47)

1. For monographs, see: (a) Pain, D. L.; Peart, B. J.; Wooldridge, K. R. H. Comprehensive Heterocyclic Chemistry, Vol. 6; Potts, K. T.; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, 175.
2. (b) Chapman, R. F.; Peart, B. J. Comprehensive Heterocyclic Chemistry II, Vol. 3; Shinkai, I.; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, 371.
3. (a) 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.
4. (b) Vicini, P.; Mazza, P. Farmaco 1989, 44, 511.
5. (c) Zani, F.; Mingiardi, M. R.; Maggiali, C. A.; Mazza, P. Farmaco 1996, 51, 707.
6. (d) Alvarez-Sanchez, R.; Basketter, D.; Pease, C.; Lepoittevin, J.-P. Chem. Res. Toxicol. 2003, 16, 627.
7. Davis, M. Adv. Heterocycl. Chem. 1972, 14, 43.
8. (a) Ponci, R.; Gialdi, F.; Baruffmi, A. Farmaco 1964, 19, 254.
9. (b) Davis, M. Adv. Heterocycl. Chem. 1972, 14, 58.
10. (c) Baggaley, K. H.; English, P. D.; Jennings, L. J. A.; Morgan, B.; Nunn, B.; Tyrrell, A. W. R. J. Med. Chem. 1985, 28, 1661.
11. (d) Vicini, P.; Amoretti, L.; Ballabeni, V.; Tognolini, M.; Barocelli, E. Bioorg. Med. Chem. 2000, 8, 2355.
12. (e) Zlotin, S. G.; Kislitsin, P. G.; Podgursky, A. I.; Samet, A. V.; Semenov, V. V. J. Org. Chem. 2000, 65, 8439.
13. (a) Wang, H.-M.; Huang, H.-Y.; Kang, I.-J.; Chen, L.-C. Heterocycles 2001, 55, 1231.
14. (b) Kang, I.-J.; Wang, H.-M.; Huang, H.-Y.; Chen, L.-C. J. Chin. Chem. Soc. 2001, 48, 1185;
15. Chem. Abstr. 2002, 137, 33248.
16. (c) Correa, A.; Tellitu, I.; Domínguez, E.; SanMartín, R. Org. Lett. 2006, 8, 4811.
17. (a) Shimizu, M.; Kikumoto, H.; Konakahara, T.; Gama, Y.; Shibuya, I. Heterocycles 1999, 51, 3005.
18. (b) Shimizu, M.; Takeda, A.; Fukazawa, H.; Abe, Y.; Shibuya, I. Heterocycles 2003, 60, 1855.
19. (a) Jin, C. K.; Moon, J.-K.; Lee, W. S.; Nam, K. S. Synlett 2003, 1967.
20. (b) Sano, T.; Takagi, T.; Gama, Y.; Shibuya, I.; Shimizu, M. Synthesis 2004, 1585.
21. (a) Kikugawa, Y.; Kawase, M. Chem. Lett. 1990, 581.
22. (b) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053.
23. (c) Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartín, R. Tetrahedron Lett. 2003, 44, 3483.
24. (d) Wardrop, D. J.; Burge, M. S. Chem. Commun. 2004, 1230.
25. (e) Correa, A.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartín, R. J. Org. Chem. 2005, 70, 2256.
26. (f) Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartín, R. Org. Lett. 2005, 7, 3073.
27. (g) Correa, A.; Tellitu, I.; Domínguez, E.; SanMartín, R. J. Org. Chem. 2006, 71, 3501.
28. For recent reviews on the synthetic applications of polyvalent iodine reagents, see: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
29. (b) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
30. (c) Hypervalent Iodine Chemistry; Wirth, T., Ed.; Springer-Verlag: Berlin, 2003.
31. (d) Tohma, H.; Kita, Y. Adv. Synth. Catal. 2004, 346, 111.
32. (e) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893.
33. (f) Wirth, T. Angew. Chem. Int. Ed. 2005, 44, 3656.
34. (g) Ochiai, M. In Chemistry in Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: Weinheim, 1999.
35. For our recent work on the utilization of β-oxo amide derivatives, see: (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578.
36. (b) Dong, D.; Bi, X.; Liu, Q.; Cong, F. Chem. Commun. 2005, 3580.
37. (c) Wang, Y.; Dong, D.; Yang, Y.; Huang, J.; Ouyang, Y.; Liu, Q. Tetrahedron 2007, 63, 2724.
38. Ouyang, Y.; Dong, D.; Yu, H.; Liang, Y.; Liu, Q. Adv. Synth. Catal. 2006, 348, 206.
39. 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., Ed.; Academic Press: Orlando, 1984, 297.
40. (b) Falvey, D. E. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. S.; Jones, M., Eds.; Wiley-Interscience: Hoboken, NJ, 2004, 594.
41. (a) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577.
42. (b) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazama, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739.
43. (c) Falvey, D. E.; Kung, A. C. J. Org. Chem. 2005, 70, 3127.
44. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
45. (a) Sheldon, R. A. Chirotechnologies, Industrial Synthesis of Optically Active Compounds; Dekker: New York, 1993.
46. (b) Perlmutter, P. Conjugated Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992, 114.
47. Bernasconi, C. F. Tetrahedron 1989, 45, 4017.