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15.4.2.2.1 By Ring Enlargement

DOI: 10.1055/sos-SD-015-00917

Larsen, R. D.Science of Synthesis, (200515604.

Indoles annulated at the 2,3-position are converted into quinolin-4(1H)-ones through oxidative ring opening followed by base-induced ring closure to give 2,3-ring-fused quinolin-4(1H)-ones.[‌603‌‌606‌] Treatment of 2-arylideneindolin-3-ones with sodium azide in a 1:4 mixture of sulfuric acid and acetic acid causes ring expansion to give 2-aminoquinolin-4(1H)-ones.[‌607‌] The reaction of 2-aryl-3H-indol-3-one 1-oxides (2-arylisatogens) 209 with arylacet­ylenes 210 gives 3-arylquinolin-4(1H)-ones 211 (Scheme 73).[‌608‌,‌609‌]

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