Regioselective Synthesis of the 5,6-Dihydro-4H-furo[2,3-c]pyrrol-4-one Skeleton: A New Class of Compounds

Date

2010-01-01

Author

Koza, Gani
Karahan, Emrah
Balcı, Metin

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We hereby report the first preparation of the 5,6-dihydro-4H-furo[2.3-c]pyrrol-4-one (3) and its derivatives starting from methyl 3-(methoxycarbonyl)furnan-2-acetate (8). The ester functionality connected to the methylene group was regiospecifically converted to the desired monohydrazide 9. Conversion of 9 into the acyl azide In followed by Curtius rearrangement gave the corresponding isocyanate derivative 11 (Scheme 2). Reaction of 11 with different nucleophiles produced urethane and urea derivatives (Scheme 3). Intramolecular cyclization reactions provided the target compounds (Scheme 5). Removal of the amine-protecting group formed the title compound 3.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis

URI

https://hdl.handle.net/11511/51662

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Graduate School of Natural and Applied Sciences, Article