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Thiation of Oxindoles

1969; Pharmaceutical Society of Japan; Volume: 17; Issue: 3 Linguagem: Inglês

10.1248/cpb.17.550

1347-5223

Tohru Hino, K. Tsuneoka, Masako Nakagawa, Sanya Akaboshi,

Chemical Reaction Mechanisms

The thiation of methyl substituted oxindoles (I) with phosphorous pentasulfide gave the corresponding 2-indolinethiones (II). The 2-indolinethione (II) having more than one hydrogen at 3-position, however, were sensitive towards phosphorous pentasulfide to produce the indolic compounds such as III, IV, V and VI. On the other hand the 2-indolinethione (VIII) prepared from VII with phosphorous pentasulfide, was stable towards the reagent. Reactivity of 2-indolinthione (IIb) was compared with the oxindole (Ib) in some reactions including the deuteration at 3-position in deuterochloroform-acetic acid-d4.