Mn(III)/Cu(II)-mediated radical cyclization of α-(methylthio)acetamides

Synlett

Volumn , Issue 9, 1999, Pages 1468-1470

  Ishibashi, Hiroyuki ^a   Toyao, Atsushi ^a   Takeda, Yoshifumi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Carbamoylmethyl radical; Copper(II) acetate; Manganese(III) acetate; Neophyl rearrangement; Radical cyclization

Indexed keywords

ACETAMIDE DERIVATIVE; COPPER; INDOLE DERIVATIVE; MANGANESE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON TRANSPORT; NONHUMAN; OXIDATION;

EID: 0032880098     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2876     Document Type: Article

References (25)

1. For reviews of our works on the carbamoylmethyl radical cyclizations, see Ishibashi, H.; Sato, T.; Ikeda, M. Yuki Gousei Kagaku Kyokai Shi 1995, 53, 85; Ikeda, M.; Sato, T.; Ishibashi, H. Rev. Heteroatom Chem. 1998, 18, 169.
2. For reviews of our works on the carbamoylmethyl radical cyclizations, see Ishibashi, H.; Sato, T.; Ikeda, M. Yuki Gousei Kagaku Kyokai Shi 1995, 53, 85; Ikeda, M.; Sato, T.; Ishibashi, H. Rev. Heteroatom Chem. 1998, 18, 169.
3. For recent references on the carbamoylmethyl radical cyclizations, see (a) Baker, S. R.; Parsons, A. F.; Wilson, M. Tetrahedron Lett. 1998, 39, 2815.
4. (b) Baker, S. R.; Parsons, A. F.; Pons, J.-F.; Wilson, M. Tetrahedron Lett. 1998, 39, 7197.
5. (c) Ikeda, M.; Ohtani, S.; Yamamoto, T.; Sato, T.; Ishibashi, H. J. Chem. Soc., Perkin Trans. I 1998, 1763.
6. (d) Ikeda, M.; Ohtani, S.; Sato, T.; Ishibashi, H. Synthesis 1998, 1803.
7. (e) Baker, S. R.; Burton, K. I.; Parsons, A. F.; Pons, J.-F.; Wilson, M. J. Chem. Soc., Perkin Trans. I 1999, 427.
8. (f) Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 1029.
9. (g) Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron Lett. 1998, 39, 8995.
10. (h) Cassayre, J.; Zard, S. Z. Synlett 1999, 501.
11. (i) Ikeda, M.; Teranishi, H.; Nozaki, K.; Ishibashi, H. J. Chem. Soc., Perkin Trans. I 1998, 1691.
12. (j) Parsons, A. F.; Williams, D. A. J. Tetrahedron 1998, 54, 13405.
13. (k) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. Chem. Commun. 1999, 31.
14. (l) Wang, C.; Russell, G. A. J. Org. Chem. 1999, 64, 2346.
15. (m) Attenni, B.; Cerreti, A.; D'Annibale, A.; Resta, S.; Trogolo, C. Tetrahedron 1998, 54, 12029.
16. (n) Davies, D. T.; Kapur, N.; Parsons, A. F. Tetrahedron Lett. 1998, 39, 4397.
17. (o) Musa, O. M.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1999, 64, 1022. See also references cited therein.
18. For a review on the heteroatom radical addition-cyclization reactions, see Naito, T. Heterocycles 1999, 50, pp. 505-541.
19. 2), 5.60-5.71 (1 H, m, H-4 or H-5), 5.79-5.91 (1 H, m, H-5 or H-4).
20. For a review on the Mn(III)-based oxidative free-radical cyclizations, see Snider, B. B. Chem. Rev. 1996, 96, 339. See also refs. 2m and 2n.
21. 3 promoted cyclizations of N-(cyclohex-1-enyl)-α-methoxycarbonylacetamides, but in low yields (35-52%). See ref. 2n.
22. Parker, K. A.; Spero, D. M.; Inman, K. C. Tetrahedron Lett. 1986, 27, 2833. Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. J. Org. Chem. 1987, 52, 4072. Ishibashi, H.; So, T. S.; Okochi, K.; Sato, T.; Nakamura, N.; Nakatani, H.; Ikeda, M. J. Org. Chem. 1991, 58, 95.
23. Parker, K. A.; Spero, D. M.; Inman, K. C. Tetrahedron Lett. 1986, 27, 2833. Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. J. Org. Chem. 1987, 52, 4072. Ishibashi, H.; So, T. S.; Okochi, K.; Sato, T.; Nakamura, N.; Nakatani, H.; Ikeda, M. J. Org. Chem. 1991, 58, 95.
24. Parker, K. A.; Spero, D. M.; Inman, K. C. Tetrahedron Lett. 1986, 27, 2833. Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. J. Org. Chem. 1987, 52, 4072. Ishibashi, H.; So, T. S.; Okochi, K.; Sato, T.; Nakamura, N.; Nakatani, H.; Ikeda, M. J. Org. Chem. 1991, 58, 95.
25. Stereochemistry of the methylthio group of 16 was confirmed by the fact that the oxidation of 16 with MCPBA followed by heating of the resulting sulfoxide in boiling toluene brought about a thermal syn-elimination of methanesulfenic acid. See Sato, T.; Nakamura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. I 1992, 2399.