GB1271052A - Stilbyl-1,2,3-triazole compounds - Google Patents

Abstract

1,271,052. Substituted stilbyl-1,2,3-triazoles. NIPPON KAYAKU K.K. 9 March, 1970 [7 March, 1969; 2 July, 1969], No. 11079/70. Heading C2C. [Also in Division C4] Novel substituted stilbyl-1,2,3-triazole compounds of the general formula wherein A is a benzene ring, a naphthalene ring or an acenaphthene ring in which two adjacent carbon atoms thereof constitute the two carbon atoms of the triazole ring, and in which the rings represented by A may be substituted by an alkyl radical, an alkoxy radical and/or a chlorine atom, and when A is a benzene ring a further triazole ring may be attached thereto in which two further adjacent carbon atoms of the benzene ring constitute the two carbon atoms of the further triazole ring as shown in the general formula in which B is a substituted or unsubstituted benzene or naphthalene ring, and R is -OR, or -N(R 2 )(R 3 ), in which R 1 , R 2 and R 3 are each a hydrogen atom, or an alkyl, cycloalkyl, hydroxyalkyl, alkoxyalkyl, N,N - dialkylaminoalkyl, carboxyalkyl, aralkyl or aryl radical, or R 2 and R 3 together with the nitrogen atom to which they are attached form a morpholino or piperidino radical, are prepared either by (a) oxidizing a compound of the general formula preferably in the presence of a water-soluble organic solvent, e.g. pyridine, picoline or dimethylformamide, using as oxidizing agent, for example, cupric sulphate or acetate, an alkali metal, hypohalogenide or nitrobenzene; (b) condensing a compound of the general formula with a compound of the general formula or with an anil compound of the general formula preferably in the presence of both a solvent such as dimethylformamide or dimethylsulphoxide, and a catalyst such as an alkali metal alcoholate, alkali metal phenoxide or alkali metal p-toluene sulphonic acid amide; or when preparing compounds in which R is not a hydroxyl radical, by (c) halogenizing a compound of the general formula and reacting the acid halide compound so formed with a compound of the formula R 1 OH or MN(R 2 )(R 3 ). In method (c) the halogenation is preferably chlorination using as chlorinating agent thionyl chloride, phosphorus oxychloride, phosphorous tri- or pentachloride in an inert solvent. The compound of the formula given in method (a) is preferably obtained by diazotizing a 4-amino-2-cyanostilbene of the general formula and then coupling the diazonium salt thus formed to the o-position of the amino group of an aromatic amine of the general formula The novel compounds of the invention may be used as fluorescent brightening agents for natural or synthetic fibres.