Synthesis and Some Regularities of Transformations of 5,5-Dimethyl-3-(2-methylalyl)-2-thioxo-2,3,5,6-tetrahydrobenzo[h]quinazoline-4(1H)-one. Antibacterial Activity of the Obtained Compounds

A. I. Markosyan; Маркосян Ашот Ишханович; A. S. Ayvazyan; Айвазян Ани Сережаевна; S. А. Gabrielyan; Габриелян С. А.; M. Yu. Danghyan; Дангян М. Ю.; J. A. Avakimyan; Авакимян Дж. А.; F. H. Arsenyan; Арсенян Ф. Г.

doi:10.31857/S0044460X24030083

Synthesis and Some Regularities of Transformations of 5,5-Dimethyl-3-(2-methylalyl)-2-thioxo-2,3,5,6-tetrahydrobenzo[h]quinazoline-4(1H)-one. Antibacterial Activity of the Obtained Compounds

Authors: Markosyan A.I.¹, Ayvazyan A.S.¹, Gabrielyan S.А.¹, Danghyan M.Y.¹, Avakimyan J.A.¹, Arsenyan F.H.¹
Affiliations:
1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Issue: Vol 94, No 3 (2024)
Pages: 376-384
Section: Articles
URL: https://journals.rcsi.science/0044-460X/article/view/261506
DOI: https://doi.org/10.31857/S0044460X24030083
EDN: https://elibrary.ru/FYVFMI
ID: 261506

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Abstract

Based on ethyl 1-amino-3,3-dimethyl-3,4-dihydronaphthalene-2-carboxylate (amino ester), a method for the synthesis of 5,5-dimethyl-3-(2-methylallyl)-2-thioxo-2,3,5,6-tetrahydrobenzo[h]quinazoline-4(1H)-one was developed. The latter was alkylated with halides of various structures, resulting in the production of 2-alkylsulfanyl-5,5-dimethyl-3-(2-methylallyl)-5, 6-dihydrobenzo[h]quinazoline-4(3H)-ones. By condensation of thioxobenzoquinazoline with hydrazine hydrate, 2-hydrazinyl-5,5-dimethyl-3-(2-methylallyl)-5,6-dihydrobenzo[h]quinazoline-4(3H)-one was synthesized, but similar reactions with 2-ethanolamine and 3-propanolamine proceeded abnormally with the formation of 2-(2-hydroxyethyl)amino-5,5-dimethyl-5,6-dihydrobenzo[h]quinazoline-4(3H)-one and 2-(3-hydroxypropyl)amino-5,5-dimethyl-5,6-dihydrobenzo[h]quinazoline-4(3H)-one, respectively. The interaction of the indicated thioxobenzoquinazoline with benzylamine proceeds with intramolecular cyclization with the formation of 6,6,10,10-tetramethyl-9,10-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazoline-7(6H)-one. The antibacterial properties of the synthesized compounds were studied. It was found that the studied compounds have antibacterial activity.

Keywords

condensation, thioxobenzoquinazoline, intramolecular cyclization, sulfanylsubstituted, alkylation, antibacterial activity

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