One-pot synthesis of heterocycles initiated by chemoselective reduction of bifunctional carbonyl compounds

European Journal of Organic Chemistry

Volumn , Issue 5, 2006, Pages 1117-1120

  Kato, Hirofumi ^a   Shibata, Ikuya ^a   Kanazawa, Nobuaki ^a   Yasuda, Makoto ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Heterocycles; One pot synthesis; Reduction; Tin hydride

Indexed keywords

EID: 33644765844     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500927     Document Type: Article

References (32)

1. Synthetic uses of organotin compounds. See, for example: a) A. K. Sawer, in: Organotin Compounds, Marcel Dekker: New York, 1971;
2. b) E. Negishi, in: Organometallics in Organic Synthesis; Wiley: New York; 1980, vol. 1, p. 394;
3. c) A. G. Davies, in: Organotin Chemistry; VCH, Weinheim; 1997;
4. d) I. Omae, in: Organotin Chemistry, J. Organomet. Chem. Lib. 21; Elsevier, NY 1989;
5. e) M. Pereyre, P. J. Quintard, A. Rahm, in: Tin in Organic Synthesis; Butterworth, London, 1987.
6. I. Shibata, A. Baba, Curr. Org. Chem. 2002, 6, 665-693.
7. E. W. Abel, D. A. Armitage, D. B. Brady, Trans. Faraday Soc. 1966, 62, 3459-3462.
8. Synthesis of pyrroles from 1: I. Shibata, H. Kato, N. Kanazawa, M. Yasuda, A. Baba, Synlett 2004, 137-139.
9. a) W. P. Neumann, E. Heymann, Justus Liebigs Ann. Chem. 1965, 11-23;
10. b) B.-Z. Zheng, M. Yamaguchi, H. Dei, S. Kusaka, K. Matsui, O. Yonemitsu, Tetrahedron Lett. 2000, 41, 6441-6445.
11. I. Shibata, T. Yoshida, A. Baba, H. Matsuda, Chem. Lett. 1989, 619-622.
12. T. Kawakami, T. Sugimoto, I. Shibata, A. Baba, H. Matsuda, N. Sonoda, J. Org. Chem. 1995, 60, 2677-2682.
13. A Sn-O bonds easily add to heterocumulenes: a) A. J. Bloodworth, A. G. Davies, J. Chem. Soc. 1965, 5238-5244;
14. b) A. J. Bloodworth, A. G. Davies, S. C. Vasishtha, J. Chem. Soc. C 1967, 1309-1313;
15. c) P. G. Harrison, J. J. Zuckerman, Inorg. Chem. 1970, 9, 175-181;
16. d) S. Sakai, Y. Kiyohara, K. Itoh, Y. Ishii, J. Org. Chem. 1970, 35, 2347-2350;
17. e) D. P. Agur, G. Srivastava, R. C. Mehrotra, Ind. J. Chem. 1974, 12, 1193-1196;
18. f) A. G. Davies, P. G. Harrison, J. Chem. Soc. C 1967, 1313-1317;
19. g) P. G. Harrison, J. J. Zuckerman, J. Chem. Soc. D 1969, 321a.
20. I. Shibata, H. Kato, N. Kanazawa, M. Yasuda, A. Baba, J. Am. Chem. Soc. 2004, 126, 466-467.
21. 2-Oxazolidones are important biologically active compounds and precursors of β-amino alcohols: a) M. E. Dyen, D. Swern, Chem. Rev. 1967, 67, 197-246;
22. b) S. Ozaki, Chem. Rev. 1972, 72, 457-496;
23. c) G. Cardillo, M. Orena, S. Sandri, C. Tomashini, Tetrahedron 1987, 43, 2505-2512;
24. d) A. V. R. Rao, T. G. M. Dhar, T. K. Chakraborty, M. K. Gurjar, Tetrahedron Lett. 1988, 29, 2069-2072.
25. Synthesis of heterocycles starting from terminally halogenated tin alkoxides: a) A. Baba, H. Kishiki, I. Shibata, H. Matsuda, Organometallics 1985, 4, 1329-1333;
26. b) I. Shibata, A. Baba, H. Matsuda, J. Chem. Soc. Chem. Commun. 1986, 1703-1704;
27. c) I. Shibata, K. Nakamura, A. Baba, H. Matsuda, Bull. Chem. Soc. Jpn. 1989, 62, 853-859.
28. [9]
29. 2 as a heterocumulene did not afford cyclic products, plausibly because of lower reactivity of tin-oxygen bonds than Sn-N bonds in the conjugate addition.
30. I. Shibata, A. Baba, H. Matsuda, Bull. Chem. Soc. Jpn. 1986, 59, 4000-4002.
31. a) I. Shibata, M. Nishio, A. Baba, H. Matsuda, Chem. Lett. 1993, 1219-1222;
32. b) I. Shibata, M. Nishio, A. Baba, H. Matsuda, Chem. Commun. 1993, 1067-1068.