Synthesis of 2H-1,2-benzothiazine 1,1-dioxides via heteroannulation reactions of 2-iodobenzenesulfonamide with ketone enolates under SRN1 conditions

Journal of Organic Chemistry

Volumn 70, Issue 23, 2005, Pages 9147-9155

  Layman Jr , William J ^a   Greenwood, Thomas D ^a   Downey, Aaron L ^a   Wolfe, James F ^a,b  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b EDWARD VIA COLLEGE OF OSTEOPATHIC MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; DEHALOGENATION; HYDROGEN; PHOTOCHEMICAL REACTIONS; REDUCTION; SYNTHESIS (CHEMICAL);

BUTANONE; HETEROANNULATION; PHOTOSTIMULATION; PINACOLONE; POTASSIUM ENOLATES;

KETONES;

1,2,3,4 TETRAHYDROCYCLOPENTA[C][1,2]BENZOTHIAZINE 5,5 DIOXIDE; 2 BUTANONE; 2 IODOBENZENESULFONAMIDE; 2 METHYL 3 PENTANONE; 2,4 DIMETHYL 3 PENTANONE; 2H 1,2 BENZOTHIAZINE 1,1 DIOXIDE; 3 (1 METHYLETHYL) 2H 1,2 BENZOTHIAZINE 1,1 DIOXIDE; 3 (1 METHYLETHYL) 4 METHYL 2H 1,2 BENZOTHIAZINE 1,1 DIOXIDE; 3 ETHYL 2H 1,2 BENZOTHIAZINE 1,1 DIOXIDE; 3 ETHYL 4 METHYL 2H 1,2 BENZOTHIAZINE 1,1 DIOXIDE; 3 METHYL 2H 1,2 BENZOTHIAZINE 1,1 DIOXIDE; 3 METHYLBUTAN 2 ONE; 3 PENTANONE; 3,4 DIMETHYL 2H 1,2 BENZOTHIAZINE 1,1 DIOXIDE; 8,9,10,11 TETRAHYDRO 11A HYDROXY 7H CYCLOOCTA[C][1,2]BENZOTHIAZINE 5,5 DIOXIDE; ACETIC ACID; ACETONE; ALKANONE; AMMONIA; BENZENESULFONAMIDE DERIVATIVE; BENZOTHIAZINE DERIVATIVE; CYCLOHEXANONE; CYCLOPENTANONE DERIVATIVE; HYDROGEN; KETONE; OXAZOLINE DERIVATIVE; PHENYLACETIC ACID ETHYL ESTER; POTASSIUM DERIVATIVE; TERT BUTYL ACETATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANNULATION REACTION; ARTICLE; DEHALOGENATION; ISOTOPE LABELING; PHOTOSTIMULATION; REDUCTION; SYNTHESIS;

DIOXOLES; HYDROCARBONS, HALOGENATED; KETONES; OXYGEN COMPOUNDS; SULFONAMIDES; THIAZINES;

EID: 27744506873     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050964e     Document Type: Article

References (57)

1. RN1 Mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983.
2. (b) Bowman, W. R. Chem. Soc. Rev. 1988, 17, 283.
3. (c) Rossi, R. A.; Pierini, A. B.; Palacios, S. M. In Advances in Free Radical Chemistry; Tanner, D. D., Ed.; JAI Press: Greenwich, CT, 1990; Chapter 5
4. J. Chem. Educ. 1989, 66, 720.
5. (d) Norris, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergammon: New York, 1991; Vol. 4.
6. (e) Saveant, J.-M. Tetrahedron 1994, 50, 10117.
7. (f) Rossi, R. A.; Pierini, A. B.; Penenory, A. B. In The Chemistry of Functional Groups, Suppl. D, The Chemistry of Halides, Pseudo-halides and Azides; Patai S., Rappoport, Z., Eds.; Wiley: New York, 1995; Chapter 24.
8. (g) Rossi, R. A.; Pierini, A. B.; Santiago, A. N. Org. React. 1999, 54, 1-271.
9. Beugelmans, R. Bull. Soc. Chim. Belg. 1984, 93, 547-556.
10. (a) Beugelmans, R.; Roussi, G. J. Chem. Soc., Chem. Commun. 1979, 950-951.
11. (b) Bard, R. R.; Bunnett, J. F. J. Org. Chem. 1980, 45, 1547-1548.
12. (c) Boujlel, K.; Simonet, J.; Roussi, G.; Beugelmans, R. Tetrahedron Lett. 1982, 23, 173-176.
13. (d) Beugelmans, R.; Chbani, M. Bull. Soc. Chim. Fr. 1995, 132, 306-313.
14. (a) Beugelmans, R.; Boudet, B.; Quintero, L. Tetrahedron Lett. 1980, 21, 1943-1944.
15. (b) Fontan, R.; Galvez, C.; Viladoms, P. Heterocycles 1981, 16, 1473-1474.
16. (c) Estel, L.; Marsais, F.; Quéquiner, G. J. Org. Chem. 1988, 53, 2740-2744.
17. Beugelmans, R.; Ginsburg, H. J. Chem. Soc., Chem. Commun. 1980, 508-509.
18. (a) Beugelmans, R.; Bois-Choussy, M. Synthesis 1981, 729-731.
19. (b) Beugelmans, R.; Ginsburg, H.; Bois-Choussy, M. J. Chem. Soc., Parkin Trans. 1 1982, 1149-1152.
20. (c) Beugelmans, R.; Bois-Choussy, M. Tetrahedron 1992, 48, 8285-8294.
21. (a) Beugelmans, R.; Chastanet, J.; Roussi, G. Tetrahedron Lett. 1982, 23, 2313-2314.
22. (b) Beugelmans, R.; Chastanet, J.; Roussi, G. Tetrahedron 1984, 40, 311-314.
23. (c) Beugelmans, R.; Bois-Choussy, M. J. Org. Chem. 1991, 56, 2518-2522.
24. Beugelmans, R.; Chastanet, J.; Ginsburg, H.; Quintero-Cortes, L.; Roussi, G. J. Org. Chem. 1985, 50, 4933-4938.
25. Beugelmans, R.; Ginsburg, H. Heterocydes 1985, 23, 1197-1203.
26. Beugelmans, R.; Bois-Choussy, M. Heterocydes 1987, 26, 1863-1871.
27. Beugelmans, R.; Chbani, M. Bull. Soc. Chim. Fr. 1995, 132, 729-733.
28. (a) Sianesi, E.; Redaelli, R.; Magistretti, M. J.; Massarani, E. J. Med. Chem. 1973, 16, 1133-1137.
29. (b) Lombardino, J. G. Chron. Drug Discovery 1982, 1, 173-200.
30. (c) Camoutsis, C.; Catsoulacos, P. J. Heterocycl. Chem. 1992, 29, 569-570.
31. (d) Proudfoot, J. R.; Patel, U. R.; Dyatkin, A. B. J. Org. Chem. 1997, 62, 1851-1853.
32. (a) Lombardino, J. G.; Wiseman, E. H. J. Med. Chem. 1971, 14, 973-977.
33. (b) Catsoulacos, P. J. Heterocyd. Chem. 1971, 8, 947-950.
34. (c) Hauser, C. R.; Wantanabe, H.; Mao, C.-L.; Barnish, I. T. J. Org. Chem. 1969, 34, 919-926.
35. Brown, C. A. J. Org. Chem. 1974, 39, 1324-1325.
36. Rossi, R. A.; Bunnett, J. F. J. Org. Chem. 1973, 38, 3020-3025.
37. The facile oxidation of 2d compared to that of 2c is probably due to relief of steric interactions between the C-4 methyl group in 2d and the aryl hydrogen at C-5. This oxidation process likely proceeds via epoxidation of the C-3,4 double bond leading to pyrimidalization of the C-4 carbon.
38. (a) Bunnett, J. F.; Sundberg, J. E. J. Org. Chem. 1976, 41, 1702-1706.
39. (b) Semmelhack, M. F.; Bargar, T. M. J. Org. Chem. 1977, 42, 1481-1482.
40. (c) Wolfe, J. F.; Moon, M. P.; Sleevi, M. C.; Bunnett, J. F.; Bard, R. R. J. Org. Chem. 1978, 43, 1019-1020.
41. (d) Semmelhack, M. F.; Bargar, T. M. J. Am. Chem. Soc. 1980, 102, 7765-7774.
42. 2, 18% of pure 5 was obtained.
43. It is postulated that enones 20a,b likely arise via electron-transfer steps analogous to step 7 of Scheme 3.
44. 8.
45. Quintard, J.-P.; Hauvette-Frey, S.; Pereyre, M. J. Organomet. Chem. 1978, 159, 147-164.
46. M'Halla, F.; Pinson, J.; Saveant, J. M. J. Electroanal. Chem. 1978, 89, 347-361.
47. Komin, A.; Wolfe, J. F. J. Org. Chem. 1977, 42, 2481-2486.
48. Hay, J. V.; Wolfe, J. F. J. Am. Chem. Soc. 1975, 97, 3702-3706.
49. Nair, V.; Chamberlain, S. D. J. Am. Chem. Soc. 1985, 107, 2183-2185.
50. 3 solution.
51. Wong, J.-W.; Natalie, K. J.; Nwokogu, G. C.; Pisipati, J. S.; Flaherty, P. T.; Greenwood, T. D.; Wolfe, J. F. J. Org. Chem. 1997, 62, 6152-6159.
52. Hoffman, A. K.; Feldman, A. M.; Geblum, E.; Hodgson, W. G. J. Am. Chem. Soc. 1964, 86, 639-646.
53. Leffler, J. E.; Jaffe, H. J. Org. Chem. 1975, 40, 797-799.
54. Takeuchi, Y.; Liu, Z.; Satoh, A.; Shiragami, T.; Shibata, N. Chem. Pharm. Bull. 1999, 47, 1730-1733.
55. Chau, M. M.; Kice, J. L. J. Org. Chem. 1977, 42, 3265-3270.
56. The source of the small amount of aryl deuterium at δ 7.64 and its position on the sulfonamide ring were not determined.
57. Sheldrick, G. M. SHELXTL NT, version 6.12; Bruker Analytical X-ray Systems: Inc. Madison, WI, 2001.