The Base-catalyzed Condensation of <i>o</i>-Nitropropiophenone

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<jats:title>Abstract</jats:title> <jats:p>Treatment of o-nitropropiophenone with sodium acetylide in liquid ammonia at −70°C gave a yellow phenol, C18H18O3N2, as a major product. The permanganate oxidation of the phenol gave 2-(1-carbamoylethyl)-2-methyl-3-indolinone, which was synthesized independently. From this result and the spectral data, the structure of the phenol was postulated to be 1-(o-hydroxyphenyl) derivative of the above indolinone. The neutral fraction of the reaction mixture gave three new compounds: 3-(o-Nitrophenyl)-1-pentyn-3-ol, 2-methyl-2-(2-methyl-3-indolinon-2-yl)-3(2H)-benzofuranone, and 3,3a-dihydro-2-hydroxy-3,3a-dimethyl-2-(o-nitrophenyl)-4(2H)-isoxazolo[2,3-a]indolone. Their structures were assigned from their spectral data. A mechanism for the formation of these products as well as for the base-catalyzed condensation of o-nitroacetophenone is discussed.</jats:p>

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