Annulation of ethyl [bis(ethylthio)methyl]benzoate and ethyl 2- [1,3]dithiolan-2-yl-benzoate with α,β-unsaturated carbonyl compounds: A new synthesis of naphthalene and anthracene derivatives

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 10, 1996, Pages 1785-1789

  Ozaki, Yutaka ^a   Imaizumi, Kazuhiro ^a   Okamura, Kyouko ^a   Morozumi, Masahiro ^a   Hosoya, Ayako ^a   Kim, Sang Won ^a  

^a JOSAI UNIVERSITY   (Japan)

Author keywords

anthracene; naphthalene; synthesis; tandem Michael Claisen condensation; 2C + 4C annulation

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ANTHRACENE DERIVATIVE; BENZOIC ACID DERIVATIVE; CARBONYL DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; POLYMERIZATION;

EID: 0029807793     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1785     Document Type: Article

References (21)

1. A part of this study was presented at the 111th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1991, and the 112th Annual Meeting of the Pharmaceutical Society of Japan, Fukuoka, March 1992.
2. A part of this study was presented at the 111th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1991, and the 112th Annual Meeting of the Pharmaceutical Society of Japan, Fukuoka, March 1992.
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4. b) Ozaki Y., Kim S., ibid., 37, 304-307 (1989)
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6. Ozaki Y., Mochida K., Kim S., J. Chem. Soc., Perkin Trans. 1, 1989, 1219-1224; Ozaki Y., Kubo A., Kim S., Chem. Pharm. Bull., 41, 481-483 (1993).
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12. Hauser F. M., Rhee R. P., J. Org. Chem., 43, 178-180 (1978); Broom N. J. P., Sammes P. G., J. Chem. Soc., Chem. Commun., 1978, 162-164; Wildeman J., Borgen P. C., Pluim H., Rouwette P. H. F. M., van Leusen A. M., Tetrahedron Lett., 1978, 2213-2216; Kraus G. A., Sugimoto H., ibid., 1978, 2263-2266; Hauser F. M., Prasanna S., J. Org. Chem., 44, 2596- 2598 (1979); Mpango G. B., Snieckus V., Tetrahedron Lett., 21, 4827-4830 (1980); van Leusen A. M., Tcrpstra J. W., ibid., 22, 5097-5100 (1981); Chan T. H., Prasad C. V. C., J. Org Chem., 52, 120-124 (1987).
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15. Hauser F. M., Rhee R. P., J. Org. Chem., 43, 178-180 (1978); Broom N. J. P., Sammes P. G., J. Chem. Soc., Chem. Commun., 1978, 162-164; Wildeman J., Borgen P. C., Pluim H., Rouwette P. H. F. M., van Leusen A. M., Tetrahedron Lett., 1978, 2213-2216; Kraus G. A., Sugimoto H., ibid., 1978, 2263-2266; Hauser F. M., Prasanna S., J. Org. Chem., 44, 2596- 2598 (1979); Mpango G. B., Snieckus V., Tetrahedron Lett., 21, 4827-4830 (1980); van Leusen A. M., Tcrpstra J. W., ibid., 22, 5097-5100 (1981); Chan T. H., Prasad C. V. C., J. Org Chem., 52, 120-124 (1987).
16. For a similar annulation of methyl 2-[1,3]dithian-2-yl-benzoate with α,β-unsaturated carbonyl compounds to form polycyclic systems, see Wadi A., Lopez-Calahorra F., Alvarez M., Joule J. A., Tetrahedron Lett., 33, 3679-3682 (1992).
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