Some Transformations of 4′-Amino-1′H-spiro[cycloheptane-1,2′-naphthalene]-3′-carbonitrile

Abstract— The corresponding Schiff bases were synthesized by condensation of 4′-amino-1′H-spiro[cycloheptane-1,2′-naphthalene]-3′-carbonitrile with anilines. The reaction of the indicated aminonitrile with 4-chlorobutanoyl chloride and subsequent cyclization of the intermediate amide gave rise to 2-(3-chloropropyl)-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-one, which in the presence of potassium hydroxide underwent cyclization to form 10,11-dihydro-5H-spiro[benzo[h]pyrrolo[2,1-b]quinazolin-6,1′-cycloheptane]-7(9H)-one. The reaction of the aminonitrile with ethyl-3-chloro-3-oxopropanoate and cyclization of the corresponding intermediate amide furnished ethyl 2-(4-oxo-4,6-dihydro-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-2-yl)acetate. The latter was hydrolyzed to give 2-methyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-one, further condensation of which with aromatic aldehydes afforded heterostilbenes possessing antitumor properties.