Convenient transformation of 3-alkoxyfurans to 2-alkoxy-3-furanones or cis-2-alkoxy-2-butene-1,4-diones with phenyltrimethylammonium tribromide

Heterocycles

Volumn 65, Issue 6, 2005, Pages 1347-1358

  Sayama, Shinsei ^a  

^a FUKUSHIMA MEDICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31344479881     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-10366     Document Type: Article

References (53)

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52. The yield of 2-isopropoxy-3-furanone (6a) was not fully satisfactory, with PTAB or PHPB(less than 68% yield). It was assumed that steric hindrance of the isopropoxy group predominantly exerted an influence on the decrease in reactivity of 3-alkoxy-2,4,5-triphenylfurans (3, 4). The reaction of ethoxyfurans (2) and (3) with PTAB in t-butyl alcohol did not afforded corresponding 2-t-butoxy-3-furanones for 18 h at room temperature.
53. Furil, 4-(2-furoyl)-2-butanone, and 3-(2-furoyl)propanenitrile gave no corresponding furanones with PTAB in ethyl alcohol for 14h at room temperature. 4-(2-Furoyl)-2-butanone and 3-(2-furoyl)-propanenitrile were recovered unchanged with PTAB in DMSO. Furfuryl benzoate did not give corresponding enediones in moderate yield with PTAB-DMSO. It was assumed that both 3-alkoxy substituent and 2,5-diphenyl moiety were required for the selective transformations of furans to 2-alkoxy-3(2H)-furanones and alkoxyenediones.