High-Pressure Organic Chemistry. 19. High-Pressure-Promoted, Silica Gel-Catalyzed Reaction of Epoxides with Nitrogen Heterocycles1,

Citations Over TimeTop 10% of 1996 papers

Abstract

The reaction of epoxides with nitrogen heterocycles such as indoles, pyrroles, imidazoles, and pyrazoles was studied under both high-pressure and silica gel-catalyzed conditions. Whereas it has been reported that the treatment of indole with styrene oxide at 10 kbar and 42 °C for 24 h gave 2-(3-indolyl)-2-phenylethanol in 56% yield, the same compound was obtained in 88% yield when the reaction was conducted on silica gel at rt for 1 week. Similarly, efficient reaction of epoxides with pyrroles, imidazoles, and pyrazoles was achieved. In terms of stereochemical features, the epoxide ring opening reaction of (R)-(+)-styrene oxide with indole was found to proceed stereoselectively in an SN2 fashion at the benzyl carbon, in either case.

Related Papers

• → NHC catalyzed CO2 fixation with epoxides: Probable mechanisms reveal ter molecular pathway(2011)55 cited
• → Two distinct epoxide ring opening pathways in a monocyclic model system of the kedarcidin chromophore(1998)4 cited
• → Epoxide hydrase in human liver biopsy specimens: Assay and properties(1974)55 cited
• → Microsomal Styrene Mono-oxygenase and Styrene Epoxide Hydrase Activities in Rats(1976)43 cited
• Regioselictivity in styrene oxide epoxide cycle cleavage by ethylenediamines in different solvents(2011)