GB1326890A - Phenanthrotriazolyl derivatives - Google Patents

Abstract

1326890 Phenanthrotriazoyl derivatives SANDOZ Ltd 13 Aug 1971 [14 Aug 1970] 38074/71 Heading C2C [Also in Divisions C3 C4 and D1] The invention comprises compounds of Formula I where R 1 and R 4 are independently H, Cl, F, CN, CO 2 H, SO 3 H, CONH 2 , a carboxylic acid or sulphonic acid ester radical or an alkyl- or arylsulphonyl radical, R 2 is H, CO 2 H or may form a lactone ring with R 1 , R 3 is H, F, Cl, CN, a C 1 to C 12 alkyl radical which may be substituted, a carboxylic or sulphonic acid radical, CONH 2 , a carboxylic or sulphonic acid ester radical, an alkyl- or arylsulphonyl radical, a phenyl radical which may be substituted or when R 4 and R 3 are in vicinal positions they may jointly be -CH=CH-CH=CH- and m is 1, 2 or 3 or the invention comprises compounds of Formula II where R 6 is H, CN, SO 3 H, or a sulphonic acid ester radical, R 7 is H or with R 6 forms an -O-CO- group where the CO is attached to the ethylenic carbon atom, R 8 is H, Cl, phenyl which may be substituted, a sulphonic acid aryl ester radical, a phenyl sulphonyl radical which may be substituted or with R 9 represents -CH=CH-CH=CH-, R 9 is H, R 10 is H, Cl, CN, SO 3 H, or a sulphonyl acid aryl ester radical at least one of R 8 , R 9 and R 10 being H and m is 1, 2 or 3. The compounds may be produced (a) by the oxidative cyclization of compounds of Formula II at 0‹ to 150‹ C. with an alkali or alkaline earth hypohalite, an inorganic or organic Cu II compound or air or oxygen in the presence of a Cu II compound, (b) by condensation of 1 mol of with 1 mole of where R 1 , R 3 , R 4 and m have the above meanings, one of X and Y represent an aldehyde radical and the other is -CH 2 -Z where Z is H, CN, CO 2 H, an unsubstituted amide or -PO(O alkyl) 2 , -PO(O aryl) 2 , -PO(O aryl)aryl, -PO(O alkyl)alkyl or P<SP>+</SP>aryl 3 X<SP>-</SP>, (c) by the saponification of compounds of formula I where R 2 is CN, R 1 is O alkyl or OH where the alkyl or H are cleaved and form a lactone or (d) by sulphonating or sulphohalogenating a compound of Formula III where R 1 , R 3 and R 4 are not SO 3 H, a sulphonic acid ester radical m is 1 and followed by conversion of the acid into an ester or amide. The compounds have optical brightening properties.