RAS Chemistry & Material ScienceЖурнал общей химии Russian Journal of General Chemistry

  • ISSN (Print) 0044-460X
  • ISSN (Online) 3034-5596

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

PII
10.31857/S0044460X24030083-1
DOI
10.31857/S0044460X24030083
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 94 / Issue number 3
Pages
376-384
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
конденсация тиоксобензохиназолин внутримолекулярная циклизация сульфанилпроизводные алкилирование антибактериальная активность
Date of publication
17.09.2025
Year of publication
2025
Number of purchasers
0
Views
14

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