Synthesis of new potentially antiviral furan-fused compounds by thermolysis of benzocyclobutene derivatives

Heterocycles

Volumn 62, Issue , 2004, Pages 207-211

  Matsuya, Yuji ^a   Qin, Hongbo ^a   Nagaoka, Mamiko ^a   Nemoto, Hideo ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; BENZOCYCLOBUTENE DERIVATIVE; FURAN DERIVATIVE; METHANE; O QUINODIMETHANE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 0346459985     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-s(p)52     Document Type: Article

References (10)

1. H. Nemoto and K. Fukumoto, Tetrahedron, 1998, 54, 5425.
2. (a) N. Toyooka, M. Nagaoka, H. Kakuda, and H. Nemoto, Synlett, 2001, 1123.
3. (b) N. Toyooka, M. Nagaoka, E. Sasaki, H. Qin, H. Kakuda, and H. Nemoto, Tetrahedron, 2002, 58, 6097.
4. Unpublished data. The results of the bioassay for these compounds will be reported elsewhere in near future.
5. T. Kametani, Y. Kato, T. Honda, and K. Fukumoto, J. Am. Chem. Soc., 1976, 98, 8185.
6. 3) δ: 156.10, 142.98, 136.71, 126.71, 122.97, 122.40, 121.92, 118.46, 110.30, 104.68, 79.75, 65.28, 63.65, 51.17, 35.20, 33.94, 31.28, 29.69, 17.88, 12.60.
7. The corresponding E-isomers could not be detected in all cases, and the geometries were presumed based on the reaction mechanism.
8. w = 0.109, RI = 0. 039 for I > 2.0σ(I) data).
9. The first description concerning [1,5] sigmatropic rearrangement of o-quinodimethanes; T. Kametani, M. Tsubuki, Y. Shiratori, Y. Kato, H. Nemoto, M. Ihara, and K. Fukumoto, J. Org. Chem., 1977, 42, 2672.
10. For example, removal and several transformations of the cyano group, which plays an important role for lowering LUMO energy level of the quinodimethanes in the inverse electron-demand Diels-Alder step, are being examined.