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Volumn 43, Issue 48, 2002, Pages 8715-8719

A simple and rapid entry to 5-alkyl (aryl)-5-hydroxy-3,4-diarylfuranones and 3a-hydroxy-1-aryl-2,3a,4,5-tetrahydronaphthofuranones via a tandem esterification and oxidative cyclization process

Author keywords

bromoketone; 5 hydroxyfuranone; Esterification; Oxidative cyclization; Phenylacetic acid

Indexed keywords

ACETIC ACID DERIVATIVE; ALPHA BROMOKETONE; FURANONE DERIVATIVE; KETONE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

EID: 0037175469     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02144-5     Document Type: Article
Times cited : (28)

References (36)
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    • note
    • 3S requires C, 70.98; H, 5.36%.
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    • α-Bromoketones were prepared via Friedel-Crafts acylation of the appropriate arene followed by bromination of the resulting ketone according to the similar procedure described in the literature. See for example: (a) Giordano, C.; Casagrande, F. Ger. Offen. DE 3006277, 4 Sep 1980, 26 pp, Chem. Abstr. 94:30372; (b) Carter, J. S.; Rogier, D. J.; Graneto, M. J.; Seibert, K.; Koboldt, C. M.; Zhang, Y.; Talley, J. Bioorg. Med. Chem. Lett. 1999, 9, 1167-1170.; (c) Almansa, C.; de Arriba, A. F.; Cavalcanti, F. L.; Gomez, L. A.; Miralles, A.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. J. Med. Chem. 2001, 44, 350-361.
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    • α-Bromoketones were prepared via Friedel-Crafts acylation of the appropriate arene followed by bromination of the resulting ketone according to the similar procedure described in the literature. See for example: (a) Giordano, C.; Casagrande, F. Ger. Offen. DE 3006277, 4 Sep 1980, 26 pp, Chem. Abstr. 94:30372; (b) Carter, J. S.; Rogier, D. J.; Graneto, M. J.; Seibert, K.; Koboldt, C. M.; Zhang, Y.; Talley, J. Bioorg. Med. Chem. Lett. 1999, 9, 1167-1170.; (c) Almansa, C.; de Arriba, A. F.; Cavalcanti, F. L.; Gomez, L. A.; Miralles, A.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. J. Med. Chem. 2001, 44, 350-361.
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  • 33
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    • α-Bromoketones were prepared via Friedel-Crafts acylation of the appropriate arene followed by bromination of the resulting ketone according to the similar procedure described in the literature. See for example: (a) Giordano, C.; Casagrande, F. Ger. Offen. DE 3006277, 4 Sep 1980, 26 pp, Chem. Abstr. 94:30372; (b) Carter, J. S.; Rogier, D. J.; Graneto, M. J.; Seibert, K.; Koboldt, C. M.; Zhang, Y.; Talley, J. Bioorg. Med. Chem. Lett. 1999, 9, 1167-1170.; (c) Almansa, C.; de Arriba, A. F.; Cavalcanti, F. L.; Gomez, L. A.; Miralles, A.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. J. Med. Chem. 2001, 44, 350-361.
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    • Mechanistically, the reaction proceeds via in situ generation of the phenacyl ester followed by an intramolecular aldol-type condensation leading to the formation of the corresponding furanone, which subsequently can react with molecular oxygen to yield the product. See for example: Ref. 18
    • Mechanistically, the reaction proceeds via in situ generation of the phenacyl ester followed by an intramolecular aldol-type condensation leading to the formation of the corresponding furanone, which subsequently can react with molecular oxygen to yield the product. See for example: Ref. 18 .
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.