Patent GB-1430664-A (GB)
Title: Bisoxadiazole compounds processes for their manufacture and their use
IPC: C07F9/653
Filed: 1973-10-17
Abstract: 1430664 Bis-oxadiazole derivatives CIBAGEIGY AG 17 Oct 1973 [18 Oct 1972 (2)] 48427/73 Heading C2C [Also in Division C3] The invention comprises bis-oxadiazoles of Formula I in which R<SP>1</SP> and R<SP>1</SP> 1  each independently represents a hydrogen atom, an aliphatic, cycloaliphatic or araliphatic group with up to 18 carbon atoms, which may be substituted by a non-chromaphoric substituent, or air, at most, binuclear carbocyclic or heterocyclic aromatic group which may be substituted by a non-chromophoric substituent and Q represents a group of formula in which a represents hydrogen or halogen, a C 1 -C 4  alkyl or alkoxy group, a sulphonic acid group or a salt thereof, or an optionally substituted sulphamoyl group, or both groups a together with the diphenylene group, represent a 9,10-dihydrophenanthrene ring, and the benzene ring A may be optionally substituted by a halogen atom, a C 1 -C 4  alkyl or alkoxy group, a sulphonic acid group or a salt thereof or an optionally substituted sulphamoyl group, or may possess a fused-on six-membered ring. The bis-oxadiazoles of the invention may be prepared by reacting one mol of a compound of formula simultaneously or successively with a mol each of R 1 Y 2  and R<SP>1</SP> 1 Y 2 , one of the symbols Y 1  and Y 2  being a carboxyl group or a functional derivative thereof and the other denoting a hydrazide group to give a diacylhydrazine of Formula (V) and subjecting this compound to cyclization. Compounds of Formula (IV) in which R 2  is H, optionally substituted C 1 -C 6  alkyl, C 2 -C 4  alkenyl, cyclohexyl optionally substituted by CH 3  or C 1 -C 4  alkoxy groups, optionally substituted phenyl-(C 1 -C 6 )alkyl, or optionally substituted phenyl, phenoxy, styryl, diphenylyl, naphthyl, pyridyl, quinolyl, thienyl- 2 or furyl-2 and Q 1  denotes a radical of Formula (II) or (III) above except that both radicals a together with the diphenylene radical do not represent a 9,10-dihydrophenanthene ring, may be made by first reacting a dicarboxylic acid dihalide of formula (Hal is Cl or Br) with 2 molecular proportions of a hydrazide R 2 CONHNM 2  and subjecting the resulting acylhydrazine compound to cyclization, e.g. by treatment with thionyl chloride. Compounds of Formula (I) may also be made by reacting one mole of a compound Z 1 QZ 1  with one of a compound of Formula VI or Formula VII and where appropriate subsequently saponifying and decarboxylating the carboxylic acid derivatives first produced; in these formulae one of Z 1  and Z 2  is a CHO group and the other represents a CH 3  group, a  group or a functional derivative thereof or a group of formulae or -CH=P(R) 3  in which R is a C 1 -C 5  alkyl or phenyl. Compounds of formula may also be reacted with compounds of Formula (VIII) or of Formula IX or to react compounds of Formula (X) or of Formula (XI) with compounds of formula n which V is methyl, -CH 2 COOH or a functional derivative thereof or one of the phosphorus-containing groups. Numerous examples of the products are given and they are stated to be optical brightening agents for natural and synthetic fabrics and fibres, and polymers.