Novel one-pot preparation of 5-methoxylated indoline and indole derivatives using a hypervalent iodine(III) reagent

Heterocycles

Volumn 51, Issue 8, 1999, Pages 1785-1788

  Tohma, Hirofumi ^a   Watanabe, Hiroaki ^a   Takizawa, Shinobu ^a   Maegawa, Tomohiro ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; IODINE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; SYNTHESIS;

EID: 0033179859     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8605     Document Type: Article

References (37)

1. (a) M. Ochiai, Rev. Heteroatom Chem., 1989, 2, 92;
2. (b) R. M. Moriarty and R. K. Vaid, Synthesis , 1990, 431;
3. (c) R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365;
4. (d) A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers Inc., New York, 1992;
5. (e) Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113;
6. (f) P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123;
7. (g) A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997;
8. (h) T. Kitamura and Y. Fujiwara, Org. Prep. Proc. Int., 1997, 29, 409.
9. (a) J. D. White, G. Caravatti, T. B. Kline, and E. Edstrom, Tetrahedron, 1983, 39, 2393;
10. (b) A. V. Rama Rao, M. K. Gurjar, and P. A. Sharma, Tetrahedron Lett., 1991, 32, 6613;
11. (c) S. Wang, B. D. Gates, and J. S. Swenton, J. Org. Chem., 1991, 56, 1979;
12. (d) Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka, and T. Yakura, J. Am. Chem. Soc., 1992, 114, 2175;
13. (e) A. Pelter, R. S. Ward, and A. Abd-el-Ghani, J. Chem. Soc., Perkin Trans. 1, 1996, 1353;
14. (f) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, and T. Takada, J. Org. Chem., 1998, 63, 6625;
15. (g) Y. Kita, M. Egi, and H. Tohma, Chem. Commun., 1999, 143.
16. K. H. Pausacker, J. Chem. Soc., 1953, 1989.
17. G. B. Barlin, K. H. Pausacker, and N. V. Riggs, J. Chem. Soc., 1954, 3122.
18. P. B. Kokil, S. D. Patil, T. Ravidranathan, and P. M. Nair, Tetrahedron Lett., 1979, 989.
19. P. Magnus, J. Lacour, and W. Weber, J. Am. Chem. Soc., 1993, 115, 9347.
20. V. V. Zhdankin, A. P. Krasutsky, C. J. Kuehl, A. J. Simonsen, J. K. Woodward, B. Mismash, and J. T. Bolz, J. Am. Chem. Soc., 1996, 118, 5192.
21. V. V. Zhdankin, M. McSherry, B. Mismash, J. T. Bolz, J. K. Woodward, R. M. Arbit, and S. Erickson, Tetrahedron Lett., 1997, 38, 21.
22. V. V. Zhdankin, C. J. Kuehl, A. P. Krasutsky, J. T. Bolz, B. Mismash, J. K. Woodward, and A. J. Simonsen, Tetrahedron Lett., 1995, 36, 7975.
23. R. Barret and M. Daudon, Tetrahedron Lett., 1991, 32, 2133.
24. R. M. Moriarty and O. Prakash, Adv. Heterocyclic Chem., 1998, 69, 1.
25. P. Dalidowicz and J. S. Swenton, J. Org. Chem., 1993, 58, 4802.
26. T. A. Engler, W. Chai, and K. O. LaTessa, J. Org. Chem., 1996, 61, 9297.
27. (a) K. S. Feldman, M. M. Bruendl, and K. Schildknegt, J. Org. Chem., 1995, 60, 7722;
28. (b) K. S. Feldman, M. M. Bruendl, K. Schildknegt, and A. C. Bohnstedt, J. Org. Chem., 1996, 61, 5440.
29. (a) Y. Kita, M. Egi, A. Okajima, M. Ohtsubo, T. Takada, and H. Tohma, Chem. Commun., 1996, 1491;
30. (b) Y. Kita, M. Egi, M. Ohtsubo, T. Saiki, T. Takada, and H. Tohma, Chem. Commun., 1996, 2225;
31. (c) T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, and Y. Kita, J. Org. Chem., 1998, 63, 7698.
32. N-Tosylaniline was found to proceed more efficiently than N-acetylaniline; the reaction of N-acetyl-4-anisidine with 2d yielded the corresponding indole (36%) and 3-hydroxy-4-anisidine (33%). Thus, the choice of protective group plays an important role for the yield of products.
33. We examined the reactions of 1a and 2d respectively with PIFA. N-Tosyl-2-hydroxyanisidine (35%) and N-tosyl-4-hydroxyaniline (28%) were obtained immediately by the reaction of 1a with PIFA. On the other hand, the oxidation of 2d with PIFA gave predominantly phenylthioacet-aldehyde (58%) via the iodine-olefin complex.
34. 4S 423.1504, found 423.1501.
35. 3 and H-2. (formula presented)
36. N-Tosylaniline was prepared from commercially available anilines. A variety of phenyl vinyl sulfide derivatives except for commercially available 2d were readily prepared by literature's procedures; see: (a) P. A. Magriotis, T. J. Doyle, and K. D. Kim, Tetrahedron Lett., 1990, 31, 2541;
37. (b) P. A. Magriotis, J. T. Brown, and M. E. Scott, Tetrahedron Lett., 1991, 32, 5047.