Revisiting the addition of nitriloxides on protoanemonin. A new access to (2 E)-3-(3′-arylisoxazol-5′-yl) propenoic acids

C Roussel, R Fihi, K Ciamala, P Audebert…

Index: Roussel, Christophe; Fihi, Rachid; Ciamala, Kabula; Audebert, Pierre; Vebrel, Joel New Journal of Chemistry, 2000 , vol. 24, # 6 p. 471 - 476

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Citation Number: 11

Abstract

Some 4-substituted arylnitriloxides undergo 1, 3-dipolar cycloadditions with 5-methylene (5H) furan-2-one (protoanemonin) with formation of spiroisoxazolines. These spiroadducts can be opened to the corresponding (2E)-3-(3′-arylisoxazol-5′-yl) propenoic acids 5 and 3-aryl-5 [4′-(3′-aryl-4′, 5′-dihydroisoxazolinyl)] isoxazole 6 by various ways, including acidic and basic treatments, as well as electrooxidation. In the latter case, the electron ...