2-Amino-3-cyano-4,5-dimethylfuran as Precursors to Butenolides and Arylacetic Acids
Year: 1989
Type: article
Abstract: A facile synthesis of butenolides and arylacetic acids via a Michael reaction of the title compound at C(5) is reported.1 While investigating the feasibility for utilizing various furan %-aminonitriles (e.g., A , Scheme I) as dienes in Diels-Alder cycloaddition reactions with monoactivated dienaphiles to synthesize highly substituted 2-aminobenronitriles ($), we have now observed that certain dienophiles produce Michael product ( 2 ) rather than the expected eycloadduet ( 3 ) .In contrast with the reaction between maleic anhydride and 4,5-disubstituted 2-amino-3-cyanofurans, which gave 2-aminobenronitriles from Diels-Alder adducrs,2 s series of doubly activated dienophiles have been found to undergo predominately a Michael reaction at C-5.3 The resulting products (e.g., 5 ) may be utilized to synthesize various bas'-butenolides and arylacetic acids.These compounds are of ~ignificant interest co researchers looking for synthetic routes to natural products containing the unsaturated lactone and possessing biological activity.'The procedures also represent new routes
Source: Heterocycles
DOI: 10.3987/com-89-4927
Institution: University of Georgia
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W2951971594