A convenient modification of the Gassman oxindole synthesis

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4631-4634

  Wright, Stephen W ^a   McClure, Lester D ^a   Hageman, David L ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

aniline; cyclization; oxalyl chloride; oxindole; sulfoxide

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030200406     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00920-3     Document Type: Article

References (29)

1. 1. For recent reviews, see: (a) Gribble, G. W. Contemp. Org. Chem. 1994, 1, 145-172;
2. (b) Ellis, G. P. in The Chemistry of Heterocyclic Compounds; Wiley: Chichester, 1992; vol 47, part 2.
3. (c) Sundberg, R. J. in Comprehensive Heterocyclic Chemistry, ed. Katritzky, A. R.; Rees, C. W.; Cheeseman, G. W. H.; Pergamon: Oxford, 1984; vol 4, pp 313-376.
4. 2. (a) Beckett, A. H.; Daisley, R. W.; Walker, J. Tetrahedron 1968, 24, 6093-6109;
5. (b) Sumpter, W. C. Chem. Rev. 1945, 37, 443-479.
6. 3. Radical processes: (a) Zard, S. Z.; Boivin, J.; Yousfi, M. Tetrahedron Lett. 1994, 35, 9553-9556;
7. (b) Zard, S. Z.; Axon, J.; Boiteau, L.; Boivin, J.; Forbes, J. E. Tetrahedron Lett. 1994, 35, 1719-1722;
8. (c) Jones, K.; Wilkinson, J.; Ewin, R. Tetrahedron Lett. 1994, 35, 7673-7676. Nitrenium ion processes: Kikugawa, Y.; Shimada, M. Chem. Letters 1987, 1771-1774. Organolithium processes: Clark, R. D.; Muchowski, J. M.; Fisher, L. E.; Flippin, L. A.; Repke, D. B.; Souchet, M. Synthesis 1991, 871-878. Photochemical processes: Yonemitsu, O.; Hamada, T.; Okuno, Y.; Ohmori, M.; Nishi, T. Chem. Pharm. Bull. 1981, 29, 128-136.
9. (c) Jones, K.; Wilkinson, J.; Ewin, R. Tetrahedron Lett. 1994, 35, 7673-7676. Nitrenium ion processes: Kikugawa, Y.; Shimada, M. Chem. Letters 1987, 1771-1774. Organolithium processes: Clark, R. D.; Muchowski, J. M.; Fisher, L. E.; Flippin, L. A.; Repke, D. B.; Souchet, M. Synthesis 1991, 871-878. Photochemical processes: Yonemitsu, O.; Hamada, T.; Okuno, Y.; Ohmori, M.; Nishi, T. Chem. Pharm. Bull. 1981, 29, 128-136.
10. (c) Jones, K.; Wilkinson, J.; Ewin, R. Tetrahedron Lett. 1994, 35, 7673-7676. Nitrenium ion processes: Kikugawa, Y.; Shimada, M. Chem. Letters 1987, 1771-1774. Organolithium processes: Clark, R. D.; Muchowski, J. M.; Fisher, L. E.; Flippin, L. A.; Repke, D. B.; Souchet, M. Synthesis 1991, 871-878. Photochemical processes: Yonemitsu, O.; Hamada, T.; Okuno, Y.; Ohmori, M.; Nishi, T. Chem. Pharm. Bull. 1981, 29, 128-136.
11. (c) Jones, K.; Wilkinson, J.; Ewin, R. Tetrahedron Lett. 1994, 35, 7673-7676. Nitrenium ion processes: Kikugawa, Y.; Shimada, M. Chem. Letters 1987, 1771-1774. Organolithium processes: Clark, R. D.; Muchowski, J. M.; Fisher, L. E.; Flippin, L. A.; Repke, D. B.; Souchet, M. Synthesis 1991, 871-878. Photochemical processes: Yonemitsu, O.; Hamada, T.; Okuno, Y.; Ohmori, M.; Nishi, T. Chem. Pharm. Bull. 1981, 29, 128-136.
12. 4. Cyclization of ortho-aminophenylacetates: (a) Hardegger, E.; Corrodi, H. Helv. Chim. Acta 1956, 39, 514-517;
13. (b) Hardegger, E.; Corrodi, H.; Romeo, H. Helv. Chim. Acta 1955, 38, 463-467. See also Ref. 2a. Reduction of isatins: Crestini, C.; Saladino, R. Synth. Commun. 1994, 24, 2835-2841.
14. (b) Hardegger, E.; Corrodi, H.; Romeo, H. Helv. Chim. Acta 1955, 38, 463-467. See also Ref. 2a. Reduction of isatins: Crestini, C.; Saladino, R. Synth. Commun. 1994, 24, 2835-2841.
15. 5. (a) Gassman, P. G.; Gruetzmacher, G.; van Bergen, T. J. J. Am. Chem. Soc. 1974, 96, 5512-5517;
16. (b) Gassman, P. G.; van Bergen, T. J. J. Am. Chem. Soc. 1974, 96, 5508-5512;
17. (c) Gassman, P. G.; Gruetzmacher, G.; van Bergen, T. J. J. Am. Chem. Soc. 1974, 95, 6508-6509.
18. 13 is frequently contaminated with other chlorides of sulfur, chlorine, and HCl.
19. 13 is frequently contaminated with other chlorides of sulfur, chlorine, and HCl.
20. 7. Wright, S. W.; Abelman, M. M.; Bostrom, L. L.; Corbett, R. L. Tetrahedron Lett. 1992, 33, 153-156.
21. 8. (a) van Asten, J. J. A.; Louw, R. Tetrahedron Lett. 1975, 16, 671-674;
22. (b) Coppola, G. M.; Hardtmann, G. E. J. Heterocycl. Chem. 1979, 16, 1605-1610.
23. 2, 5% Pd/C, EtOH, 45 psig, 20 °C; mp 80-82 °C.
24. (b) Erlenmeyer, H.; Grubenmann, W.; Bloch, H. Helv. Chim. Acta 1948, 31, 75-77; HCl salt mp 244-246 °C.
25. 2, 5% Pd/C, EtOH, 45 psig, 25 °C.
26. 11. Swern, D.; Omura, K.; Sharma, A. K. J. Org. Chem. 1976, 41, 957-962. Other sulfoxide "activating" agents that have been reported to be effective in DMSO oxidations were not examined in the present work.
27. 12. Walsh, D. A.; Moran, H. W.; Shamblee, D. A.; Uwaydah, I. M.; Welstead, W. J.; Sancilio, L. F.; Dannenburg, W. N. J. Med. Chem. 1984, 27, 1379-1388.
28. 13. Warpehoski, M. A.; Bradford, V. S. Tetrahedron Lett. 1994, 27, 2735-2738.
29. 14. Walker, J.; Daisley, R. W.; Beckett, A. H. J. Med. Chem. 1970, 13, 983-985.