Acylation of 3,5-dimethoxyaniline (I) with 4-methoxyphenylacetyl chloride (II) afforded amide (III). Treatment of (III) with Vilsmeier reagent gave rise to 2-chloroquinoline derivative (IV), which was hydrolyzed to quinolinone (V) using aqueous HOAc. Conjugate addition to (V) of acrylonitrile (VI) produced the cyanoethyl quinolinone (VII). The title tetrazole was then obtained by reaction of nitrile (VII) with tributyltin azide in hot toluene.
The cyclization of 3,5-dimethoxyaniline (I) with 2-formyl-2-(4-methoxyphenyl)acetic acid ethyl ester (II) by means of polyphosphoric acid trimethylsilyl ester (PPSE) by heating at 110 C gives the quinolone (III), which is alkylated with vinyl cyanide (IV) by means of Triton B in DMF to yield the propionitrile derivative (V). Finally, the cyano group of (V) is converted into the target tetrazolyl derivative by cyclization with tri-tert-butylstannyl azide in refluxing toluene.