Abstract
3-Isocyanoisobenzofuran-1(3<i>H</i>)-ones (phthalides) were prepared in two steps from the corresponding phthalaldehydic acids. The 3-isocyanoisobenzofuran-1(3<i>H</i>)-ones are readily rearranged to the corresponding 3-cyanoisobenzofuran-1(3<i>H</i>)-ones using triflic anhydride and 2,6-lutidine, thus enabling the synthesis of 3-cyanoisobenzofuran-1(3<i>H</i>)-ones without using toxic cyanide. Furthermore their annulation with Michael acceptors results in direct formation of 1,4-naphthoquinols/1,4-naphthoquinones in moderate yields.
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