Synthesis of optically active 1,4-benzoxazinones and 1,5- benzoxazepinones by regiocontrolled ring transformations of oxirane carboxylic acids and esters with aromatic o-hydroxyarylamines

Tetrahedron

Volumn 55, Issue 30, 1999, Pages 9205-9220

  Woydowski, Karsten ^a   Liebscher, Jürgen ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOXAZINONE; 1,5 BENZOXAZEPINONE; AMINE; BENZOXAZINONE DERIVATIVE; CARBOXYLIC ACID; ESTER; ETHYLENE OXIDE; OXAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; DECOMPOSITION; ENANTIOMER; OPTICAL ROTATION; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033597990     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00488-3     Document Type: Article

References (29)

1. Woydowski, K.; Fleischhauer, J.; Schiffer, J.; Liebscher, J. J. Chem. Soc., Perkin Trans 1 1999, 149-153.
2. Culvenor, C. C.; Davies, W.; Heath, N. S. J. Chem. Soc. 1949, 278-282.
3. Inoue, H.; Nagao, T. Cronicels of Drug Discovery, American Chemical Society, 1993, 207-237.
4. Woydowski, K.; Ziemer, B.; Liebscher, J. Tetrahedron Asymmetry 1998, 9, 1231-1237.
5. Woydowski, K.; Liebscher, J. Synthesis 1998, 1110-1112.
6. Chong, J. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1563-1564.
7. Weber, F. G.; Giese, H.; Köppel, H.; Reinhold, M.; Ströbel, R. J. Prakt. Chem. 1985, 327, 133-143.
8. Möhrle, H.; Schaltenbrandt, R. Pharmazie 1985, 40, 387-39.
9. Teller, J. in Houben-Weyl, Methoden der Organischen Chemie (Editor E. Schaumann), Vol. E 9a, p. 141, Thieme Verlag Stuttgart, 1997.
10. Freedman, H. H.; Frost, A. E. J. Org. Chem. 1958, 23, 1292-1298.
11. Einhorn, A.; Ruppert, E. Liebigs Ann. Chem. 1902, 325, 305-339.
12. Bischoff, C. A. Ber. Dtsch. Chem. Ges. 1897, 30, 2926-2930.
13. Zahn, O. J. Prakt. Chem. 1900, 61, 532-544
14. Andreichikov, Yu. S.; Varkentin, L. I.; Pitirimova, S. G.; Vilenchik, Ya. M. Khim. Geterotsikl. Soedin. 1977, 1126-1128.
15. Bartsch, H.; Schwarz, O. J. Heterocycl. Chem. 1983, 20, 45-48.
16. Biekert, E.; Hoffmann, D.; Meyer, F. J. Chem. Ber. 1961, 94, 1676-1682.
17. Rüfenacht, K.; Kristinsson, H.; Mattern, G. Helv. Chim. Acta 1976, 59, 1593-1613.
18. Clausson-Kaas, N.; Heide, H.; Olsen, G. Acta Chem Scand. 1969, 23, 2322-2324.
19. Clausson-Kaas, N.; Ostermayer, F.; Renk, C.; Deuss, R. US-Patent 452528 (1965), Chem. Abstr. 1968, 69, 96746.
20. Bonsignore, L.; Cabiddu, S.; Loy, G.; Secci, M. J. Heterocycl. Chem. 1982, 19, 1241-1242.
21. Hashiyama, T.; Watanabe, A.; Inoue, H.; Konda, M.; Takeda, M.; Murata, S.; Nagao, T. Chem. Pharm. Bull. 1985, 33, 634-641.
22. Bhalerao, U. T., Thyagarajan, G. Indian J. Chem. 1969, 7, 429-433.
23. Evans, D.; Lockhard, I. M. J. Chem. Soc. 1965, 4806-4812.
24. Levai, A.; Ott, J.; Snatzke, G. Monatsh. Chem. 1992, 123, 919-930.
25. Mori, K.; Iwasawa, H. Tetrahedron 1980, 36, 87-90.
26. Petit, Y.; Sanner, C.; Larcheveque, M. Synthesis 1988, 538-540.
27. Petit, Y.; Larcheveque, M. Org. Synthesis 1997, 75, 37-48.
28. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
29. Full details have been deposited at: Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen, whence this material can be obtained on quoting a full literature citation and the deposition number CSD 410682.