Year: 1955
Type: article
Abstract: Aromatic thiocyano compounds were prepared in order to make a comparative examination of their antibacterial, ascaricidal, and insecticidal actions, toxicity in mice, and relationship between chemical structure and biological actions. Several of the synthetic methods were examined and following procedures were adopted. Aminophenol, toluidine, anthranilic acid, and naphthylamines were substituted with a thiocyano radical according to the Kaufmann method, and further applied with phenyl isocyanate, ammonium thiocyanate, and phosgene from which phenylurea, thiourea, and phenylthiourea derivatives of these compounds were obtained. The new compounds synthesized were 2-hydroxy-4-thiocyanophenylurea, 2-hydroxy-4-thiocyanophenylthiourea, 2, 2′-dihydroxy-4, 4′-dithiocyanodiphenylurea, and 4-thiocyanonaphthyl-(1)-thiourea. Attempted substitution of thiocyano group into the ortho-position of the amino group invariably resulted in cyclization to a thiazole ring and 2-phenylureidonaphtho [2′, 1′:4, 5] thiazole and 2-thioureidonaphtho [2′, 1′:4, 5] thiazole were obtained.
Source: YAKUGAKU ZASSHI
Authors: Taro Kaneko, Hisatora Kuroda, Toyoko Ueda
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W2605772214