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Phthalide and 1,3-indandione. IV. The synthesis of new amino derivatives of 2-phenyl- and 2-(α-naphthyl)-1,3-indandiones

M. Furdík, P. Hrnčiar, and E. Poláková

Komenský University, Bratislava

Abstract: cf. C.A. 53, 3167f. The synthesis of new amino- and acetamido derivs. of benzylidenephthalide and of α-naphthalide, of 2-phenyl-and 2-naphthyl)-1,3-indandiones is described. The NH₂ or H₂NCO group is located on the benzene or naphthalene ring licin the 4'-position. By reduction with metallic Fe or FeSO₄.7H₂O of 4'-nitrobenzylidenephthalide or 4'-nitro-α-naphthalide, 4'-aminobenzylidenephthalide (I), m. 228-9° (K.ovrddot.ofler), and 4'-amino-α-naphthalide (II), m. 222-3°, were prepd. By reduction with Fe of 2-(4'-nitrophenyl)-1,3-indandione and of 2-(4'-nitro-α-naphthyl)-1,3-indandione or by alcoholate conversion of I and II with Na metal 2-(4'-aminophenyl)-1,3-indandione, m. 198°, and 2-(4'-amino-α-naphthyl)-1,3-indandione, m. 230°, were prepd. By acetylation of I and II, 4'-acetamidobenzylidenephthalide (III), m. 285.5-6.5°, and 4'-acetamido-α-naphthalide (IV), m. 282-2.5°, were prepd. By alcoholate conversion of III and IV with Na metal 2-(4'-acetamidophenyl)-1,3-indandione, m. 232°, and 2-(4-'acetamido-α-naphthyl)-1,3-indandione, m. 225°, were prepd. In agreement with theory there is a considerably higher speed of conversion with I than with 4'-nitrobenzylidenephthalide.

Full paper in Portable Document Format: 1211a642.pdf (in Slovak)

Chemical Papers 12 (11) 642–650 (1958)