Synthesis and characterization of [1]benzopyrano[4,3-d][1,3]benzooxazocin- 13-one and its derivatives

Synlett

Volumn , Issue 17, 2006, Pages 2791-2794

  Wang, Jen Fei ^a   Liao, Yuan Xiu ^a   Kuo, Pei Yu ^a   Gau, Yung Her ^a   Yang, Ding Yah ^a  

^a TUNGHAI UNIVERSITY   (Taiwan)

Author keywords

Bicyclic compounds; Heterocycles; Ring closure; Ring opening; Steric hindrance

Indexed keywords

4 METHOXYBENZENE; [1]BENZOPYRANO[4,3 D][1,3]BENZOOXAZOCIN 13 ONE; BENZENE DERIVATIVE; BENZOPYRAN DERIVATIVE; BRIDGED COMPOUND; HETEROCYCLIC COMPOUND; NITROGEN; OXAZOCINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL STRUCTURE; RING OPENING; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33750522019     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950267     Document Type: Article

References (20)

1. Tröger, J. J. Prakt. Chem. 1887, 36, 225.
2. Demeunynck, M.; Tatibouet, A. Recent Developments in Tröger's Base Chemistry, In Progress in Heterocyclic Chemistry, Vol. 11; Gribble, G. W.; Gilchrist, T. L., Eds.; Pergamon: Oxford, UK, 1999, 1.
3. Bailly, C.; Laine, W.; Demeunynck, M.; Lhomme, J. Biochem. Biophys. Res. Commun. 2000, 273, 681.
4. Johnson, R. A.; Gorman, R. R.; Wnuk, R. J.; Crittenden, N. J.; Aiken, J. W. J. Med. Chem. 1993, 36, 3202.
5. (a) Harmata, M.; Kahraman, M. Tetrahedron: Asymmetry 2000, 11, 2875.
6. (b) Blaser, H. U.; Jalett, H. P.; Lottenbach, W.; Studer, M. J. Am. Chem. Soc. 2000, 122, 12675.
7. Levkin, P. A.; Strelenko, Y. A.; Lyssenko, K. A.; Schurig, V.; Kostyanovsky, R. G. Tetrahedron: Asymmetry 2003, 14, 2059.
8. Chen, J. S.; Watson, W. H.; Kagan, J.; Agdeppa, D. A.; Chen, S.-A. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1978, 34, 3627.
9. Molina, P.; Arques, A.; Tarraga, A.; del Rosario Obon, M. Tetrahedron 1998, 54, 997.
10. Stoncius, S.; Butkus, E.; Zyilinskas, A.; Larsson, K.; Ohrstrom, L.; Berg, U.; Warnmark, K. J. Org. Chem. 2004, 69, 5196.
11. Naemura, K.; Fukunaga, R.; Komatsu, M.; Yamanaka, M.; Chikamatsu, H. Bull. Chem. Soc. Jpn. 1989, 62, 83.
12. Harmata, M.; Murray, T. J. Org. Chem. 1989, 54, 3761.
13. Harmata, M.; Kahraman, M. Tetrahedron Lett. 1999, 40, 4133.
14. +].
15. +].
16. Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. Tetrahedron 1997, 53, 9715.
17. Huang, J. L.; Liu, H. G.; Yang, D. Y. Bioorg. Med. Chem. Lett. 2003, 13, 927.
18. Chen, D. U.; Kuo, P. Y.; Yang, D. Y. Bioorg. Med. Chem. Lett. 2005, 15, 2665.
19. Crystallographic data (excluding structure factors) for 6a and 16a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC-263524 and CCDC-263525, respectively. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.
20. Kimber, M. C.; Try, A. C.; Painter, L.; Harding, M. M.; Turner, P. J. Org. Chem. 2000, 65, 3024.