One-pot synthesis of 2,3-disubstituted naphtho[2,3-b]thiophene-4,9-diones from a 2-sulfenyl-1,4-naphthoquinone and enamines

Chemistry Letters

Volumn , Issue 6, 1999, Pages 503-504

  Kobayashi, Kazuhiro ^a   Furuta, Yoshihisa ^a   Matsuoka, Hideki ^a   Uchida, Masaharu ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033241965     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.503     Document Type: Article

References (31)

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5. This is a modification of the Kakisawa's method, which gives 3-methylnaphtho[2,3-b]furan-4,9-diones from 2-acetoxy-1,4-naphtho-quinones and an enamine derived from propanal; H. Kakisawa and Y. Inouye, Tetrahedron Lett., 1969, 1929; H. Kakisawa and M. Tateishi, Bull. Chem. Soc. Jpn., 43, 824 (1970); M. Tateishi, T. Kusumi, and H. Kakisawa, Tetrahedron, 27, 237 (1971).
6. This is a modification of the Kakisawa's method, which gives 3-methylnaphtho[2,3-b]furan-4,9-diones from 2-acetoxy-1,4-naphtho-quinones and an enamine derived from propanal; H. Kakisawa and Y. Inouye, Tetrahedron Lett., 1969, 1929; H. Kakisawa and M. Tateishi, Bull. Chem. Soc. Jpn., 43, 824 (1970); M. Tateishi, T. Kusumi, and H. Kakisawa, Tetrahedron, 27, 237 (1971).
7. This is a modification of the Kakisawa's method, which gives 3-methylnaphtho[2,3-b]furan-4,9-diones from 2-acetoxy-1,4-naphtho-quinones and an enamine derived from propanal; H. Kakisawa and Y. Inouye, Tetrahedron Lett., 1969, 1929; H. Kakisawa and M. Tateishi, Bull. Chem. Soc. Jpn., 43, 824 (1970); M. Tateishi, T. Kusumi, and H. Kakisawa, Tetrahedron, 27, 237 (1971).
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16. T. Kikuchi, A. Maruyama, N. Ohtani, S. Nagahara, H. Tanaka, T. Sakakibara, and T. Tanaka, Eur. Patent 466094 (1992); Chem. Abstr., 116, 245248d (1992); E. Fischer-Reimann, Eur. Patent 592366 (1994); Chem. Abstr., 121, 108509d (1994); T. Shibata, T. Suzuki, A. Kinoshita, and H. Hayata, Jpn. Patent 15881 (1997); Chem. Abstr., 126, 231511d (1997).
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19. V. Weinmayr, J. Am. Chem. Soc., 74, 4353 (1952); H. Tagawa and K. Ueno, Chem. Pharm. Bull., 26, 1384 (1973); M. Watanabe and V. Snieckus, J. Am. Chem. Soc., 102, 1457 (1980); A. Acosta, P. de la Cruz, P. De Miguel, E. Diez-Barra, A. de la Hoz, F. Langa, M. Majdoub, N. Martin, C. Sanchez, and C. Seoane, Tetrahedron Lett., 36, 2165 (1995).
20. V. Weinmayr, J. Am. Chem. Soc., 74, 4353 (1952); H. Tagawa and K. Ueno, Chem. Pharm. Bull., 26, 1384 (1973); M. Watanabe and V. Snieckus, J. Am. Chem. Soc., 102, 1457 (1980); A. Acosta, P. de la Cruz, P. De Miguel, E. Diez-Barra, A. de la Hoz, F. Langa, M. Majdoub, N. Martin, C. Sanchez, and C. Seoane, Tetrahedron Lett., 36, 2165 (1995).
21. V. Weinmayr, J. Am. Chem. Soc., 74, 4353 (1952); H. Tagawa and K. Ueno, Chem. Pharm. Bull., 26, 1384 (1973); M. Watanabe and V. Snieckus, J. Am. Chem. Soc., 102, 1457 (1980); A. Acosta, P. de la Cruz, P. De Miguel, E. Diez-Barra, A. de la Hoz, F. Langa, M. Majdoub, N. Martin, C. Sanchez, and C. Seoane, Tetrahedron Lett., 36, 2165 (1995).
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23. The only report on the generation of this mercapto quinone and its use in organic synthesis has been recorded by one of the present authors; H. Suginome, K. Kobayashi, A. Konishi, H. Sakurai, and H. Minakawa, J. Chem. Soc., Chem. Commun., 1993, 807.
24. For recent synthetic elaborations of 2-sulfenyl-1,4-naphthoquinones, see: W.-B. Kang, T. Sekiya, T. Toru, and Y. Ueno, J. Chem. Soc., Perkin Trans. I, 1990, 441; K. Nakagawa, Chem. Express, 6, 177 (1991); M. A. Brimble, E. Ireland, and S. J. Phythian, Tetrahedron Lett., 32, 6417 (1991); M. A. Brimble and E. Ireland, J. Chem. Soc., Perkin Trans. I, 1994, 3109; C.-P. Chuang and S.-F. Wang, Heterocycles, 43, 2215 (1996).
25. For recent synthetic elaborations of 2-sulfenyl-1,4-naphthoquinones, see: W.-B. Kang, T. Sekiya, T. Toru, and Y. Ueno, J. Chem. Soc., Perkin Trans. I, 1990, 441; K. Nakagawa, Chem. Express, 6, 177 (1991); M. A. Brimble, E. Ireland, and S. J. Phythian, Tetrahedron Lett., 32, 6417 (1991); M. A. Brimble and E. Ireland, J. Chem. Soc., Perkin Trans. I, 1994, 3109; C.-P. Chuang and S.-F. Wang, Heterocycles, 43, 2215 (1996).
26. For recent synthetic elaborations of 2-sulfenyl-1,4-naphthoquinones, see: W.-B. Kang, T. Sekiya, T. Toru, and Y. Ueno, J. Chem. Soc., Perkin Trans. I, 1990, 441; K. Nakagawa, Chem. Express, 6, 177 (1991); M. A. Brimble, E. Ireland, and S. J. Phythian, Tetrahedron Lett., 32, 6417 (1991); M. A. Brimble and E. Ireland, J. Chem. Soc., Perkin Trans. I, 1994, 3109; C.-P. Chuang and S.-F. Wang, Heterocycles, 43, 2215 (1996).
27. For recent synthetic elaborations of 2-sulfenyl-1,4-naphthoquinones, see: W.-B. Kang, T. Sekiya, T. Toru, and Y. Ueno, J. Chem. Soc., Perkin Trans. I, 1990, 441; K. Nakagawa, Chem. Express, 6, 177 (1991); M. A. Brimble, E. Ireland, and S. J. Phythian, Tetrahedron Lett., 32, 6417 (1991); M. A. Brimble and E. Ireland, J. Chem. Soc., Perkin Trans. I, 1994, 3109; C.-P. Chuang and S.-F. Wang, Heterocycles, 43, 2215 (1996).
28. For recent synthetic elaborations of 2-sulfenyl-1,4-naphthoquinones, see: W.-B. Kang, T. Sekiya, T. Toru, and Y. Ueno, J. Chem. Soc., Perkin Trans. I, 1990, 441; K. Nakagawa, Chem. Express, 6, 177 (1991); M. A. Brimble, E. Ireland, and S. J. Phythian, Tetrahedron Lett., 32, 6417 (1991); M. A. Brimble and E. Ireland, J. Chem. Soc., Perkin Trans. I, 1994, 3109; C.-P. Chuang and S.-F. Wang, Heterocycles, 43, 2215 (1996).
29. G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz, and R. Terrell, J. Am. Chem. Soc., 85, 207 (1963).
30. The reactions with equimolar amount of the enamines gave the products in somewhat diminished yields.
31. +, 46), 255 (100).