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16.10.2.1.1 Method 1: From Benzofuran Derivatives

DOI: 10.1055/sos-SD-016-00385

Haider, N.; Holzer, W.Science of Synthesis, (200416333.

Ring-enlargement reactions of 3-hydroxyisobenzofuran-1(3H)-ones 61 are frequently employed in the synthesis of phthalazin-1(2H)-ones 62 (Scheme 25).[‌78‌,‌146‌,‌188‌‌191‌] As compounds 61 (R2=H) are tautomeric with 2-formylbenzoic acids, phthalazinone synthesis from in situ prepared 3-hydroxyisobenzofuran-1(3H)-ones 61 is described in Section 16.10.1.1.1.1.2 (Scheme 14). The syntheses of 61 mostly start from the corresponding phthalic anhydrides, but follow different pathways depending on the substitutents, particularly R2 at the 3-position.[‌188‌‌190‌] 3-Bromoisobenzofuran-1(3H)-ones can also be used as starting materials, which are hydrolyzed to the 3-hydroxy compounds 61 under the cyclization reaction conditions[‌131‌‌133‌,‌192‌‌194‌] [see also Section 16.10.1.1.1.1.2 (Scheme 14)].

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