Dehydrogenation by air: Preparation of 1,3-disubstituted-5,1-dioxo- 5,10-dihydro-1H-benzo[g] isochromene scaffold

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2459-2462

  Wang, Wuyi ^a   Breining, Tibor ^b   Li, Tiechao ^a   Milburn, Robert ^c   Attardo, Giorgio ^a  

^a Shire Canada   (Canada)

^b Diagnostic Chemicals Limited   (Canada)

^c UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CHROMENE DERIVATIVE; ISOCHROMAN DERIVATIVE; PEROXIDE; PYRAN DERIVATIVE;

AIR; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; OXIDATION;

EID: 0032560021     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00287-1     Document Type: Article

References (17)

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4. b. Kraus, G. A. and Li, J. J. Org. Chem. 1994, 59, 2219-2222;
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7. b. Xu, Y.-C.; Lebeau, E.; Attardo, G.; Myers, P. L. and Gillard, J. J. Org. Chem. 1994, 59, 4868-4874.
8. 4. The sequence was also suitable for isochromans carrying various groups at C-3. For example, quinones 10 and 14 were thus prepared.
9. 5. Richard C. Larock, Comprehensive Organic Transformations 1989 VCH publisher, page 129-137.
10. 6. Ravi Kumar, V.T.; Swaminathan, S. and Rajagopalan, K. J. Org. Chem. 1985, 50, 5867-5869.
11. 7. For other application of base-mediated quinone oxidation such as oxidative decyanation, see : Parker, K.A. and Kallmerten, J.L. Tetrahedron Lett. 1979, 1997-1800.
12. 1 oxide: Dowd, P.; Ham, S. W. and Geib, S. J. J. Am. Chem. Soc. 1991, 113, 7734-7743.
13. 9. Welch, S. C.; Levine, J. A. and Arimilli, M. N. Syn. Comm. 1993, 23, 131-134.
14. 10. A general procedure was described in: Attardo, G.; Xu, Y.-C.; Lavallee, J.-F.; Rej, R. and Belleau, B. PCT Int. Appl. WO 91 19725, 1991.
15. 11. These chiral templates were obtained from the respective chiral isochromans of 1 (resolved using Evan's auxiliary). The absolute configuration was determined by relating to the isochroman derived from commercially available chiral glycidol and 1,4-dimethoxyl benzene.
16. 12. Formation of B type quinonoid cation was proposed previously : Aldersley, M. F. ; Dean, F. M. and Hamzah, S. Tetrahedron Lett. 1986, 27, 255-258.
17. 13. Unpublished results.