Synthesis of spiro[1,4-benzothiazine-2,2'-pyrans] starting from methyl β-d-arabino-2-hexulopyranosonate

Journal of Heterocyclic Chemistry

Volumn 36, Issue 2, 1999, Pages 457-460

  Andersch, Jens ^a   Sicker, Dieter ^a   Wilde, Horst ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

METHYL BETA DEXTRO ARABINO 2 HEXULOPYRANOSONATE; METHYL GROUP; PYRAN DERIVATIVE; SPIRO[1,4 BENZOTHIAZINE 2,2' PYRAN]; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGENATION; SYNTHESIS;

EID: 0032954671     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360220     Document Type: Article

References (21)

1. P. Fahrni, and T. Siegfried, Hoffmann-La Roche, EP 133,493 (1985); Chem. Abstr., 103, 178578c (1985).
2. W. N. Haworth, and E. L. Hirst, J. Chem. Soc., 1858 (1926);
3. W. N. Haworth, E. L. Hirst, and A. Learner, J. Chem. Soc., 1040 (1927);
4. C. G. Anderson, W. Charlton, W. N. Haworth, and V. S. Nicholson, J. Chem. Soc., 1337 (1929);
5. H. L. Wolfram, W. W. Binkley, W. L. Shilling, and H. W. Hilton, J. Am. Chem. Soc., 73, 3553 (1951).
6. M. Bobek, J. Farkas, and F. Sorm, Collect. Czech., Chem. Commun., 32, 3572 (1967);
7. H. Ohle, Ber., 67, 155 (1934).
8. S. Kirrbach, R.-R. Schnelle, S. Hauptmann, G. Mann, H. Wilde, D. Sicker, and U. Stottmeister, J. Prakt. Chem., 334, 537 (1992).
9. A. G. M. Barrett, W. W. Doubleday, K. Kasdorf, M. Pena, G. J. Tustin, and J. A. Willardsen, J. Heterocyclic Chem., 33, 1545 (1996).
10. M. T. Fletcher, and W. Kitching, Chem. Rev., 95, 798 (1995).
11. M. Matsumoto, M. Kirihara, T. Yoshino, and T. Katho, S. Terashima, Tetrahedron Letters, 34, 6289 (1993).
12. T. M. Krülle, C. Fuente, K. A. Watson, M. Gregoriou, L. N. Johnson, K. E. Tsitsanou, S. E. Zographos, N. G. Oikonomakos, and G. W. J. Fleet, Synlett, 211 (1997).
13. M. Ueno, M. Amemiya, T. Someno, T. Masuda, and H. Iinuma, J. Antibiot., 1658 (1993).
14. A. J. Birch, R. A. Massy-Westropp, R. W. Rickards, J. Chem. Soc., 3717 (1956).
15. D. Sicker, H. Hartenstein, and M. Kluge, Natural Benzoxazinoids - Synthesis of Acetal glucosides, Aglucones, and Analogues, in: Recent Research Developments in Phytochemistry, Vol 1, S.G. Pandalai, ed, Research Signpost, Trivandrum, 1997, p 203.
16. M. Kluge and D. Sicker, Tetrahedron, 52, 10389 (1996).
17. D. Sicker and H. Hartenstein, Synthesis, 771 (1993).
18. D. Sicker, H. Hartenstein, R. Hazard, and A. Tallec, J. Heterocyclic Chem., 31, 809 (1994).
19. M. Kluge and D. Sicker, J. Heterocyclic Chem., 33, 1623 (1996).
20. H. Ohle and R. Wolter, Ber., 63, 843 (1930).
21. M. Major and W. J. Cook, J. Am. Chem. Soc., 58, 2477 (1936).