Synthesis of New Derivatives of 5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione


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5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione reacted with cyclohexyl and benzyl (4-aminophenyl)carbamates in boiling ethanol in the presence of a catalytic amount of glacial acetic acid to give the corresponding Schiff bases, cyclohexyl and benzyl (4-{[(E)-1-(4-hydroxy-2,6-dioxo-3,6-dihydro-2H-1,3-thiazin-5-yl)ethylidene]amino}phenyl)carbamates. Heating of the latter in dimethylformamide for 2 h was accompanied by evolution of COS with the formation of cyclohexyl and benzyl {4-[6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]phenyl}carbamates. The condensation of the title compound with benzene-1,2-diamine in propan-2-ol, followed by addition of 5-arylfuran-2-carbaldehyde and trifluoroacetic acid afforded 5-(2-{5-[4-bromo(nitro)phenyl]furan-2-yl}-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-4-hydroxy-2H-1,3-thiazine-2,6(3H)-diones. 5-((E)-3-{5-[4-Bromo(nitro)phenyl]furan-2-yl}prop-2-enoyl)-4-hydroxy-2H-1,3-thiazine-2,6(3H)-diones were synthesized by condensation of 5-acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione with 5-[4-bromo(nitro)phenyl]furan-2-carbaldehydes in chloroform in the presence of catalytic amounts of pyridine and piperidine.

作者简介

A. Velikorodov

Astrakhan State University

编辑信件的主要联系方式.
Email: avelikorodov@mail.ru
俄罗斯联邦, Astrakhan, 414000

A. Zukhayrayeva

Astrakhan State University

Email: avelikorodov@mail.ru
俄罗斯联邦, Astrakhan, 414000

V. Osipova

Southern Scientific Center

Email: avelikorodov@mail.ru
俄罗斯联邦, Rostov-on-Don, 34400

M. Polovinkina

Astrakhan State Technical University

Email: avelikorodov@mail.ru
俄罗斯联邦, Astrakhan, 414056

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