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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

A. I. MarkosyanScientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, ArmeniaA. S. AyvazyanScientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, ArmeniaS. А. GabrielyanScientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, ArmeniaS. S. MamyanScientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, ArmeniaA. A. AyvazyanScientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, ArmeniaA. G. ArakelyanScientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, Armenia

2023en

ABI

Annotatsiya

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.

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Identifikatorlar

DOI: 10.1134/s1070363223030040

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