Synthesis, Some Transformations, and Antibacterial Activity of 5H-Spiro[benzo[h][1,2,4]triazolo[3,4-b]quinazoline-6,1′-cycloheptane]-7(11H)-ones
Abstract
Abstract Condensation of 2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-one with hydrazine hydrate afforded 2-hydrazinyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-one. The reaction of the latter with orthoformic acid ethyl ester or carbon disulfide yielded 5H-spiro[benzo[h][1,2,4]triazolo[3,4-b]quinazoline-6,1′-cycloheptane]-7(11H)-one and 9-mercapto-5H-spiro[benzo[h][1,2,4]triazolo[3,4-b]quinazoline-6,1 ′-cycloheptane]-7(11H)-one, respectively. Alkylation of the latter with methyl and ethyl iodides, allyl bromide, and benzyl chloride gave 9-sulfanyl-substituted 5H-spiro[benzo[h][1,2,4]triazolo[3,4-b]quinazoline-6,1′-cycloheptane]-7(11H)-ones. The synthesized compounds exhibited antibacterial properties.