| 摘要 |
1,139,607. Azole compounds. CI.BA Ltd. 27 Sept., 1966 [4 Oct., 1965], No. 43047/66. Heading C2C. [Also in Divisions C3 and D1] Novel compounds of the Formula Ib wherein A represents an aromatic carbocyclic residue condensed with the azole ring, X represents -O- or -NQ- (where Q stands for hydrogen, alkyl, hydroxyalkyl, cyanoalkyl, aralkyl or sulphonylalkyl), each of the substituents R 1 , R 2 and R 3 represent hydrogen or an alkyl or alkoxy group of up to 4 carbon atoms and B 1 represents a 5- or 6-membered aromatic carbocyclic or heterocyclic residue are prepared by reacting 3-B 1 -5-R 1 -6-R 2 -8-R 3 -coumarin-7- carboxylic acid or -carboxylic acid halide with an aminobenzene, the nucleus of which is represented by A substituted in the o-position by -XH, and then heating to effect cyclization between 150‹ and 300‹ C. in the presence of a high-boiling inert organic solvent and preferably a cyclization catalyst. B 1 is preferably a thiophene, furan or pyridine residue or a benzene nucleus substituted by hydrogen atoms, alkyl or alkoxy groups of up to 7 carbon atoms, halogen atoms, carboxyl groups, carboxylic acid ester or amide groups, nitrile groups, sulphonic acid or sulphonic acid ester or amide group, or a sulphinic acid ester group up to a maximum of 4 substituents. The residue A is preferably a benzene nucleus substituted by hydrogen atoms, halogen atoms, alkyl or alkoxy groups, carboxyl groups, carboxylic acid esters, amides or nitriles, alkyl groups of up to 7 carbon atoms further substituted by carboxyl groups, carboxylic acid esters, amides or nitriles, phenyl or phenylalkyl groups, substituted amino groups, sulphonic acid groups, sulphonic acid alkyl and aryl ester groups, sulphonamide groups, sulphinic acid alkyl and aryl ester groups, or 2 adjacent substituents may form a 6-membered carbocycle fused with the benzene nucleus. More preferably, the nucleus in A may be substituted by alkyl groups of 1 to 8 carbon atoms, e.g. tert.- butyl, alkoxy groups of 1 to 4 carbon atoms, chlorine, a carboxylic group, especially an alkyl ester or amide, a phenyl group, a phenylalkyl group containing up to 10 carbon atoms, or an alkyl group of 1 to 8 carbon atoms substituted by a nitrile or carboxylic acid alkyl ester group. The compounds of the invention are used as optical brighteners for organic materials. 3 - Phenyl - coumarin - 7 - carboxylic acid is prepared by reacting 4-carboxy-2-hydroxybenzaldehyde with benzylcyanide in the presence of piperidine and water. |
