キノリン誘導体についてその12 : p-Amino-halogenophenylthiocyanateおよび6-Halogeno-8-aminoquinoline-5-thiocyanate並びにそのAzo誘導体の合成

概要

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1) 6-Iodo-8-nitroquinoline (V) was synthesized from 2-nitro-4-iodoaniline by the Skraup reaction and reduced with stannous chloride and hydrochloric acid to the amino compound (VI). These amino compounds (VI, VII, VIII) and m-iodoaniline were thiocyanated by treatment with ammonium thiocyanate and bromine in acetic acid. These thiocyanates (IX to XII), 5-thiocyanato-8-aminoquinoline, and p-thiocyanatoaniline were diazotized and reacted with phenol or m-halophenol in weakly alkaline or neutral reaction to form the azo compounds (XII to XIX). On the other hand, compounds XXV and XXVI were synthesized from I and II by the application of p-toluenesulfonyl chloride in pyridine, and XXVII and XVII by the application of acetic anhydride to III and IV. 2) Synthesis of 5-thiocyanato-6-chloro-8-hydroxyquinoline was attempted by the diazotization of 6-chloro-8-aminoquinoline to XXI and its thiocyanation with ammonium thiocyanate and bromine in acetic acid or with calcium thiocyanate in acetic acid but XXI was recovered. Consequently, XXI was nitrated in the cold to the nitro compound (XXII), reduced with Raney nickel and hydrazine to the amino compound (XXIII), and submitted to the Sandmeyer reaction to obtain XXIV. Antifungal activities of these synthesized compounds against Candida and Trichophyton were tested.
公益社団法人日本薬学会の論文
1966-03-25