キノリン誘導体について その10

抄録

1) 4-Thiocyanato-1-naphthylamine (I), 5-thiocyanato-8-aminoquinoline (II), 5-amino-6-chloroquinoline (IV), 4-nitronaphthylamine (V), and 5-thiocyanato-6-chloro-8-aminoquinoline (III) were each diazotized and reacted with potassium thiocyanate and copper thiocyanate to prepare 1, 4-bis (thiocyanato) naphthalene (VII), 5, 8-bis (thiocyanato) quinoline (IX), 5-thiocyanato-6-chloroquinoline (VI), 1-nitro-4-thiocyanatonaphthalene (VIII), and 5, 8-bis(thiocyanato)-6-chloroquinoline (X).
Nitration of 8-acetamidoquinoline with sulfuric and nitric acid mixture afforded 5-nitro-8-acetamidoquinoline (XI), whose structure was ascertained by the formation of 5-nitroquinoline from XI by its hydrolysis, diazotization, and deamination. Application of potassium chlorate to XI and 5-nitro-8-aminoquinoline (XII) in hydrochloric acid solution afforded 5-nitro-7-chloro-8-aminoquinoline (XIII) from XII but XI was recovered unchanged. Diazotization of XII and XIII, followed by treatment with potassium thiocyanate and copper thiocyanate afforded 5-nitro-8-thiocyanate and copper thiocyanate afforded 5-nitro-8-thiocyanatoquinoline (XIV) and 5-nitro-7-chloro-8-thiocyanatoquinoline (XV), respectively. Anti-candida effect of these compounds was carried out.
2) p-Thiocyanatoaniline and 3-chloro-4-thiocyanatoaniline were diazotized and reaction with phenol, or with o- or m-chlorophenol in neutral or weakly alkaline solution to prepare the compounds XVIII to XXI. Anti-candida effect of these compounds was also tested.