Synthesis of 1-(Alkoxycarbonyl)methylene-1,3-dihydroisobenzofurans and 4-(Alkoxycarbonyl)benzo[c]pyrans by Palladium-Catalysed Oxidative Carbonylation of 2-Alkynylbenzyl Alcohols, 2-Alkynylbenzaldehydes and 2-Alkynylphenyl Ketones

European Journal of Organic Chemistry

Volumn , Issue 3, 2004, Pages 574-585

  Bacchi, Alessia ^a   Costa, Mirco ^a   Cà, Nicola Della ^a   Fabbricatore, Marcella ^b   Fazio, Alessia ^b   Gabriele, Bartolo ^b   Nasi, Cristina ^a   Salerno, Giuseppe ^b  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Carbonylation; Cyclisation; Heterocycles; Palladium

Indexed keywords

1 (CARBONYL)METHYLENE 1,3 DIHYDROISOBENZOFURAN DERIVATIVE; 4 (CARBONYL)BENZO[C]PYRAN DERIVATIVE; ALKYNE; BENZALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZOPHENONE DERIVATIVE; BENZOPYRAN DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; CARBON; CARBON MONOXIDE; CARBONYL DERIVATIVE; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; HYDROXYL GROUP; IODIDE; METHANOL; OXYGEN; PALLADIUM; PALLADIUM IODIDE; POTASSIUM IODIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL BOND; CYCLIZATION; OXIDATION; REACTION ANALYSIS; SYNTHESIS; TRIPLE BOND;

EID: 1242286057     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300577     Document Type: Article

References (20)

1. B. Gabriele, M. Costa, G. Salerno, G. P. Chiusoli, J. Chem. Soc., Perkin Trans. 1 1994, 83-87.
2. B. Gabriele, G. Salerno, M. Costa, G. P. Chiusoli, J. Organomet. Chem., 2003, 687, 219-228.
3. S. Berteina, A. De Mesmaeker, Synlett 1998, 1227-1230.
4. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785-6786.
5. For a discussion on stereoelectronic effects on cyclisation reactions, see: E. E. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994, pp. 684-685.
6. P. G. Sammes, D. J. Weller, Synthesis 1995, 1205-1222.
7. N. Asao, T. Nogami, K. Takahashi, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 764-765.
8. 2] as catalyst and 1,4-benzoquinone as oxidizing agent, to give cyclic ketals or cyclic orthoester derivatives through the intermediate formation of the corresponding hemiketals has been reported recently: [8a] K. Kato, Y. Yamamoto, H. Akita, Tetrahedron Lett. 2002, 43, 4915-4917.
9. [8b] K. Kato, Y. Yamamoto, H. Akita, Tetrahedron Lett. 2002, 43, 6587-6590.
10. Dihydroisobenzofurans have found application as synthetic intermediates for the synthesis of biologically active compounds. See, for example: D. S. Brown, M. C. Elliott, C. J. Moody, T. J. Mowlem, J. Chem. Soc., Perkin Trans. 1 1995, 1137-1144.
11. Some benzo[c]pyran derivatives have shown interesting pharmacological activity. See, for example: [10a] M. R. Michaelides, R. Schoenleber, S. Thomas, D. M. Yamamoto, D. R. Britton, R. MacKenzie, J. W. Kebabian, J. Med. Chem. 1991, 34, 2946-2953.
12. [10b] M. P. DeNinno, R. Schoenleber, R. J. Perner, L. Lijewski, K. E. Asin, D. R. Britton, R. MacKenzie, J. W. Kebabian, J. Med. Chem. 1991, 34, 2561-2569.
13. B. Gabriele, G. Salerno, A. Fazio, R. Pittelli, Tetrahedron 2003, 59, 6251-6259.
14. [12a] M. Katsuya, I. Nobuharu, J. Am. Chem. Soc. 1998, 120, 1928-1929.
15. [12b] W. B. Austin, N. Bilow, W. J. Kellenghan, K. S. Y. Lau, J. Org. Chem. 1981, 46, 2280-2286.
16. [12c] S. W. Zhang, T. Sugioka, S. Takahashi, J. Mol. Catal. A., Chem. 1999, 143, 211-218.
17. [12d] K. R. Roesch, R. C. Larock, J. Org. Chem. 2002, 67, 86-94.
18. [12e] G. Dyker, W. Stirner, G. Henkel, Eur. J. Org. Chem. 2000, 1433-1441.
19. [12f] J. W. Herndon, Y. Zhang, J. Organomet. Chem. 2001, 634, 1-4.
20. [12g] M. Shindo, Y. Sato, K. Shishido, J. Org. Chem. 2001, 63, 7818-7824.