Synthesis and properties of new derivatives of 3-benzylspiro[benzo[h]quinazoline-5,1'-cycloheptane]-4(6H)-one

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Abstract

Condensation of 3-benzyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cycloheptane]-4(6H)-one with 5,5-dialkyl-2-chloromethylbenzo[h]quinazolines were used to synthesize dibenzo[h]quinazoline compounds in which spiro[benzo[h]quinazoline-5,1'-cycloheptane] in the second position is linked via a -SCH2- linker to another benzo[h]quinazoline molecule. The specified 2-thioxobenzo[h]quinazoline, under similar conditions, upon reaction with methylene iodide, forms 2,2'-[(methylenebis(sulfandiyl)]bis{3-benzyl-3H-spiro[benzo[h]quinazoline-5,1'-cycloheptane]}-4(6H)-one. A transition was made from the starting benzo[h]quinazoline to the 2-hydrazinoderivative, which is cleaved in the presence of caustic potash to form 3-benzyl-3H-spiro[benzo[h]quinazoline-5,1'-cycloheptane]-4(6H)-one. Based on the 2-hydrazino derivative, hydrazone, thiosemicarbazide, and 4-benzyl-4H-spiro[benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1'-cycloheptanones] have been synthesized. Condensation of 4-benzyl-1-mercapto-4H-spiro[benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1'-cycloheptane]-5(7H)-one with alkyl halides 1-sulfanyl-substituted triazolobenzo[h]quinazoline derivatives of various structures were obtained. The antibacterial properties of the synthesized compounds were studied.

About the authors

A. I. Markosyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of NAS RA

Email: ashot@mаrkosyan.am
prosp. Azatutyun, 26, Yerevan, 0014 Armenia

A. S. Ayvazyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of NAS RA

prosp. Azatutyun, 26, Yerevan, 0014 Armenia

S. A. Gabrielyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of NAS RA

prosp. Azatutyun, 26, Yerevan, 0014 Armenia

S. S. Mamyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of NAS RA

prosp. Azatutyun, 26, Yerevan, 0014 Armenia

R. E. Muradyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of NAS RA

prosp. Azatutyun, 26, Yerevan, 0014 Armenia

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