COMPOUNDS USEFUL IN FLUOROMETRY

摘要

1433093 Reaction of substituted dihydrofuranones with primary amino-group-containing materials F HOFFMANN-LA ROCHE & CO AG 4 March 1974 [5 March 1973] 9592/74 Heading C2C [Also in Divisions A5 C3 C4 C6 and G1] Materials containing primary amino groups having one or more than two carbon atoms are reacted with compounds of the Formula I where R 1 is a C 1 -C 8 alkyl or phenyl (C 1 -C 8 alkyl) group, R 2 is phenyl or substituted phenyl and R 3 is substituted or unsubstituted phenyl, naphthyl or indolyl, the substituents in each case being selected from halogen, C 1 -C 8 alkyl, CF 3 , C 1 -C 8 alkoxy, -NO 2 and -CN, to form novel products. Exemplified primary amino group-containing materials are primary amines, amino acids, peptides, proteins, viruses and unicellular and multicellular organisms. The reaction of the compound of Formula I with the primary amino group containing material introduces a fluorescent label into the material. The compounds of Formula I are prepared by a multistep process comprising epoxidizing a compound of formula under basic conditions to yield an epoxy ketone of formula followed by treatment with a strong anhydrous base to yield a diketone of formula The diketone is then converted into an enamine of formula where R 4 and R 5 are independently C 1 -C 8 alkyl groups and R 4 and R 5 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic ring which may contain an oxygen atom or a further nitrogen atom, by reaction with an aminomethenylating agent, followed by conversion to a hydroxy furanone of formula by basic aqueous hydrolysis and further conversion to compounds of Formula I by treatment with an alcohol of Formula R1 1 OH.