US 4,283,538 A · Novel triarylmethane compounds

Abstract

In one embodiment, the present invention is concerned with novel triarylmethane compounds possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is an alkyl group or a phenyl group, unsubstituted or substituted with a solubilizing group; R' is selected from ##STR2## wherein R" is methyl, unsubstituted or substituted with one or two halo groups or substituted with a phenyl, alkoxy or phenoxy group and ##STR3## wherein Y is an electron-withdrawing group; and R and R' taken with said ##STR4## represents ##STR5## In another embodiment the present invention is concerned with a method of synthesizing the aforementioned compounds by reacting, e.g., a 2-R'-3-(4'-hydroxy-1'-phenyl/naphthyl)-3-(phenyl/naphthyl)-2,3-dihydrobenz [d]isothiazole-1,1-dioxide with an alkylation reagent in the presence of base.

Claims23

Dependent claims

A compound of the formula ##STR93## wherein A is a phenyl moiety or a naphthyl moiety;

B is a 4'-oxo-1'-phenylidene moiety or a 4'-oxo-1'-naphthylidene moiety;
R is an alkyl group containing 1 to 4 carbon atoms or a phenyl group, unsubstituted or substituted with a solubilizing group selected from --SO.sub.3 H,--COOH and--OH;
R' is selected from ##STR94## wherein R" is methyl, unsubstituted or substituted with one or two halo groups or substituted with a phenyl, alkoxy containing 1 to 4 carbon atoms or phenoxy group and ##STR95## wherein Y is an electron-withdrawing group having a positive sigma value greater than 0.6 as defined by Hammett's Equation;
and R and R' taken with said --N--represents ##STR96##

1 more element

A compound of the formula ##STR101## wherein R.sup.1 is hydrogen, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms or hydroxy;

R.sup.2 and R.sup.4 each are selected from hydrogen, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms, chloro and fluoro;
R.sup.1 and R.sup.2 taken together represent the carbon atoms necessary to complete a fused benzene ring;
R.sup.3 is hydrogen;
alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms, hydroxy, -N,N-(dialkyl)amino wherein each alkyl contains 1 to 4 carbon atoms, -N,N-(w-R.sup.8 alkyl).sub.2 amino wherein R.sup.8 is halo or hydroxy and said alkyl contains 1 to 4 carbon atoms;
piperidino, pyrrolidino, N-methylpiperazino, morpholino, thiomorpholino or tetrahydro-2H,4H-1,3,6-dioxazocino;
R.sup.2, R.sup.3 and R.sup.4 taken together represent the atoms necessary to complete a fused quinolizidine ring;
R.sup.5 is hydrogen, alkyl containing 1 to 4 carbon atoms, phenyl, alkoxy containing 1 to 4 carbon atoms, chloro, fluoro or perhalomethylcarbinol;
R.sup.6 is hydrogen, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms, chloro or fluoro;
R.sup.7 is hydrogen, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms or hydroxy;
R.sup.6 and R.sup.7 taken together represent the carbon atoms necessary to complete a fused benzene ring;
R is an alkyl group containing 1 to 4 carbon atoms or a phenyl group, unsubstituted or substituted with a solubilizing group selected from --SO.sub.3 H, --COOH and --OH;
R' is selected from ##STR102## wherein R" is methyl, unsubstituted or substituted with one or two halo groups or substituted with a phenyl, alkoxy containing 1 to 4 carbon atoms or phenoxy group, and ##STR103## wherein Y is an electron-withdrawing group having a positive sigma value greater than 0.6 as defined by Hammett's Equation;
and R and R' taken with said ##STR104## represents ##STR105##

10 more elements

Dependencies are inferred from the claim text.

Novel triarylmethane compounds

Life of this patent

Novel triarylmethane compounds

Life of this patent

Abstract

Claims23