Synthesis of indole thiazole compounds as ligands for the Ah receptor

A method of synthesizing aromatic ketone compositions of formula I:

• wherein:
• R1 may be hydrogen or can be selected from the group consisting of (C1-C6)-alkyl and (C3-C7)-cycloalkyl, and wherein the alkyl group can be substituted by (C3-C7)-cycloalkyl or can be mono- or polysubstituted by an aryl group, wherein the aryl group can be mono- or polysubstituted by halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, hydroxy and nitro groups;
• R1 may be an aryl group, wherein the aryl group can be mono- or polysubstituted by halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, hydroxy and nitro groups;
• R1 may further be a protecting group;
• R2, R3, R4, R5, R6, and R7 may be the same or different and are each selected from the group consisting of hydrogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, (C1-C6)-acyl, (C1-C6)-alkoxy, alkoxycarbonyl (COOR1), halogen, benzyloxy, the nitro group, the amino group, the (C1-C4)-mono or dialkyl-substituted amino group, or an aryl group, wherein the aryl group can be mono- or polysubstituted by halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, hydroxy and nitro groups;
• X and Z may be the same or different and are each selected from the group consisting of O, S and NH;
• comprising the step of introducing a double bond into the 5 membered ring of the 4,5-dihydro-1,3-azoles moiety of a compound of the formula II:
• wherein the stereochemical centers may have R or S configuration.