Selective transformation of 3-acetyl-5-aryl-2-methylfurans using photooxygenation

Heterocyclic Communications

Volumn 6, Issue 6, 2000, Pages 529-532

  Onitsuka, Satoaki ^a   Nishino, Hiroshi ^b   Kurosawa, Kazu ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034551611     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2000.6.6.529     Document Type: Article

References (18)

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2. Qian, C.-Y.: Hirose, J.: Nishino, H.: Kurosawa, K. J. Heterocycl. Chem. 1994, 31, 1219.
3. Graziano, M. L.; Iesce, M. R.; Scarpati, R. Synthesis, 1984, 66.
4. Wasserman, H. H.; Ives, J. L. Tetrahedron 1981, 37, 1825 and references cited therein.
5. a) Bosshard, P.; Eugster, C. H. The Development of the Chemistry of Furans, 1952-1963 in Advances in Heterocyclic Chemistry; Vol. 7, Katritzky A. R.; Boulton A. J. Ed.; Academic: New York, 1966; pp 377-488.
6. b) Livingstone, R. Compounds Containing a Five-Membered Ring with One Hetero Atom of Group VI; Oxygen in Rodd's Chemistry of Carbon Compounds; Vol. IV, Part A, Coffey, S. Ed.; Elsevier: Amsterdam, 1973; pp 83-217.
7. c) Dean, F. M. Recent Advances in Furan Chemistry. Part I in Advances in Heterocyclic Chemistry; Vol. 30, Katritzky, A. R. Ed.; Academic: New York, 1982; pp 167-238.
8. d) Acheson, R. M. An Introduction to the Chemistry of Heterocyclic Compounds; Wiley: Tronto, 1976.
9. a) Lutz, R. E.; Welstead, Jr., W. J.; Bass, R. G.; Dale, J. I. J. Org. Chem. 1962, 27, 1111.
10. b) Graziano, M. L.; Iesce, M. R.; Scarpati, R. J. Chem. Soc., Perkin Trans., 1, 1980, 1955.
11. 3 (6b).
12. 4: C, 68.28; H, 5.73. Found: C, 68.57; H, 5.80.
13. Onitsuka, S.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 2000, 41, 3149.
14. 3) δ203.0, 196.3, 189.3 (C=O), 151.8 (>C=), 145.7, 133.8 (ArC),130.2 (HC=), 129.8 (2C), 128.9 (2C) (ArH), 30.7, 27.3 (Ac), 21.8 (Me).
15. a) Bunnelle, W. H. Chem. Rev. 1991, 91, 335.
16. b) Iesce, M. R.; Cermola, F.; Graziano, M. L.; Scarpati, R. J. Chem. Soc., Perkin Trans. 1, 1994, 147.
17. 4: C,67.23; H, 5.21. Found: C, 67.37; H, 5.29.
18. 1H NMR spectra was simultaneously formed. However, the products 2 and 3 could not be isolated from the reaction mixture. Although the photolysis of 2a and 3a using the UV light was also examined, 2a and 3a completely decomposed after 4 h and an intractable mixture was obtained.