Synthesis and Some Reactions of 3-Aminospiro[benzo[h]quinazoline-5,1′-cycloheptanes

Abstract

Methods have been developed for the synthesis of acyl and diacyl derivatives of 1′H-spiro[cyclo­heptane-1,2′-naphthalenes] and 2′-substituted spiro[cycloheptane-1,5′-naphtho[1,2-d][1,3]oxazin]-4′(6′H)-ones starting from ethyl 4′-amino-1′H-spiro[cycloheptane-1,2′-naphthalene]-3′-carboxylate (1) through variation of the amount of reactants, solvent nature, and reaction conditions. The reaction of amino ester 1 with hydrazine hydrate gave benzo[g]indazole derivative. 3-Amino-2-phenyl-3H-spiro[benzo[h]quinazolin-5,1′-cycloheptan]-4(6H)-one (8) and 3-amino-1H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-2,4(3H,6H)-dione (13) were syn­thesized and subjected to acylation with acetyl and benzoyl chlorides to obtain the corresponding amides. Amine 13 was converted to substituted ureas.