ChemInform Abstract: Reaction of 1-Alkylbenzimidazolium 3-Ylides with Ethyl 2,2-Dihydropolyfluoroalkanoates.

✍ Scribed by X. ZHANG; W. HUANG

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199904160

✦ Synopsis

Reaction of 1-Alkylbenzimidazolium 3-Ylides with Ethyl 2,2-Dihydropolyfluoroalkanoates.

-Reaction of the title polyfluoroalkanoates (II) with N-phenacyl-(I), N-acetonyl-(IV), N-(ethoxycarbonylmethyl)or N-(diethylaminocarbonylmethyl)benzimidazolium bromides (VI) in the presence of base proceeds by a cyclocondensation-ring extension sequence to afford pyrroloquinoxalines (III), (V) or (VII), resp., in moderate to good yields. In contrast, with the N-(cyanomethyl)benzimidazolium bromides (VIII) the ring-opened o-pyrrolylanilines (IX) are the major products while the expected pyrroloquinoxalines (X) are formed only in traces due to the reduced reactivity of the cyano group. -(ZHANG, X.;