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New method for the preparation of dibenzo[b, f][1,4]thiazepines

Takayoshi Fujii

Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku, Toyama 930–8555, Japan

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Wei Hao,

Wei Hao

Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku, Toyama 930–8555, Japan

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Toshiaki Yoshimura,

Corresponding Author

Toshiaki Yoshimura

[email protected]

Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku, Toyama 930–8555, Japan

Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku, Toyama 930–8555, JapanSearch for more papers by this author

Takayoshi Fujii,

Takayoshi Fujii

Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku, Toyama 930–8555, Japan

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Wei Hao,

Wei Hao

Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku, Toyama 930–8555, Japan

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Toshiaki Yoshimura,

Corresponding Author

Toshiaki Yoshimura

[email protected]

Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku, Toyama 930–8555, Japan

Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku, Toyama 930–8555, JapanSearch for more papers by this author

First published: 15 April 2004

https://doi.org/10.1002/hc.20010

Citations: 13

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Abstract

The S-amination of 9H-thioxanthen-9-ol (2a) and 9-substituted derivatives 2b–e (Me (b), Et (c), ⁱPr (d), Ph (e)) with O-mesitylenesulfonylhydroxylamine (MSH) was carried out. The expected product, 10-amino-9-hydroxy-9-isopropyl-9H-thioxanthenium mesitylenesulfonate (3d), was obtained in 78(%) yield from the corresponding thioxanthen(9)-ol 2d. However, in the case of 2a–c and 2e the reaction led instead to dibenzo[b,f][1,4]thiazepines 6a–c and 6e in moderate yields. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:246–250, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20010

REFERENCES

1(a) Jaques, R.; Rossi, A.; Urech, E.; Bein, H. J.; Hoffman, K. Helv Chim Acta 1959, 42, 1265–1278 and references therein;
10.1002/hlca.19590420422
CAS Web of Science® Google Scholar
(b) Warawa, E. J.; Migler, B. M.; Ohnmacht, C. J.; Needles, A. L.; Gatos, G. C.; McLaren, F. M.; Nelson, C. L.; Krikland, K. M. J Med Chem 2001, 44, 372–389 and references therein.
10.1021/jm000242+
CAS PubMed Web of Science® Google Scholar
2(a) Brodrick, C. I.; Nicholson, J. S.; Short, W. F. J Chem Soc 1954, 3857–3866;
10.1039/jr9540003857
CAS Web of Science® Google Scholar
(b) Galt, R. H. B.; Loudon, J. D. J Chem Soc 1959, 885–889.
10.1039/jr9590000885
CAS Web of Science® Google Scholar
3 Catsoulacos, P. J Heterocyclic Chem 1970, 7, 409–411.
10.1002/jhet.5570070229
CAS Web of Science® Google Scholar
4 Fujii, T.; Asai, S.; Okada, T.; Hao, W.; Morita, H.; Yoshimura, T. Tetrahedron Lett 2003, 6203–6205.
10.1016/S0040-4039(03)01547-8
CAS Web of Science® Google Scholar
5 Price, C. C.; Hori, M.; Parasara, T.; Polk, M. J Am Chem Soc 1963, 85, 2278–2282.
10.1021/ja00898a019
CAS Web of Science® Google Scholar
6 Hashimoto, T.; Kanai, K.; Kitano, H.; Fukui, K. Nippon Kagaku Zasshi 1965, 86, 438–442.
10.1246/nikkashi1948.86.438
CAS Google Scholar
7(a) Kluba, M.; Harwood, J.; Casey, P. K.; Ternary, A. L., Jr. J Heterocyclic Chem 1985, 22, 1261–1267;
10.1002/jhet.5570220524
CAS Web of Science® Google Scholar
(b) Llama, E. F.; Campo, C.; Campo, M.; Anadon, M. Eur J Med Chem 1989, 24, 391–396;
10.1016/0223-5234(89)90083-4
CAS Web of Science® Google Scholar
(c) Shukla, D.; Wan, P. J. Photochem Photobiol A 1994, 79, 55–59.
10.1016/1010-6030(93)03740-8
CAS Web of Science® Google Scholar
8 Bergman, E. D.; Rabinovitz, M. J Org Chem 1960, 25, 828–829.
10.1021/jo01075a602
Web of Science® Google Scholar
9 Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J Org Chem 1973, 38, 1239–1241.
10.1021/jo00946a045
CAS PubMed Web of Science® Google Scholar
10 Galt, R. H. B.; Loudon, J. D.; Sloan, A. D. B. J Chem Soc 1958, 1588–1592.
10.1039/jr9580001588
CAS Web of Science® Google Scholar
11 Shine, H. J.; Hughes, L. J Org Chem 1966, 31, 3142–3146.
10.1021/jo01348a013
CAS Web of Science® Google Scholar
12(a) Tamura, Y.; Nishikawa, Y.; Mukai, C.; Sumoto, K.; Ikeda, M. J Org Chem 1979, 44, 1684–1690;
10.1021/jo01324a022
CAS Web of Science® Google Scholar
(b) Tamura, Y.; Mukai, C.; Nishikawa, Y.; Ikeda, M. J Org Chem 1979, 44, 3296–3299.
10.1021/jo01333a004
CAS Web of Science® Google Scholar
13 Gassman, P. G. Acc Chem Res 1970, 3, 26–33.
10.1021/ar50025a004
CAS Web of Science® Google Scholar
14 Le Roux, J-P.; Desben, P. L.; Seguin, M. Tetrahedron Lett 1976, 3141–3144.
10.1016/S0040-4039(00)93862-0
CAS Google Scholar

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New method for the preparation of dibenzo[b, f][1,4]thiazepines

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