NATURAL SCIENCES

Journal of fundamental
and
applied researches

Synthesis of new aryl- and hetarylcarbamates and exploration of sometransformation reactions of synthesis among various heterocyclic compounds

2012. ¹4, pp. 116-126

Ionova Valentina A. - post-graduate student, Astrakhan State University, 1 Shaumyn Sq., 414000, Astrakhan, Russian Federation, org@aspu.ru

Temirbulatova Sofiya I. - Assistant, Astrakhan State Medicinal Academy, 121 Bakinskaya Str., 414000, Astrakhan, Russian Federation, olgatitova71@yandex.ru

Imasheva Nuriya M. - Ph.D. (Chemistry), Associate Professor, Astrakhan State University, 1 Shaumyn Sq., 414000, Astrakhan, Russian Federation, org@aspu.ru

Shchepetova Yekaterina V. - Ph.D. (Biology), Associate Professor, Astrakhan State University, 1 Shaumyn Sq., 414000, Astrakhan, Russian Federation, org@aspu.ru

The paper presents the results of a study of new aryl- and hetarylcarbamates synthesis. It covers alkylation with allyliodide of methyl-N-phenylcarbamate and methyl N-(2-chlorophenyl)carbamate under ’liquid-liquid’ phase-transfer catalysis conditions, and corresponding N-allyl-N-methoxycarbonyl-aminobenzenes in 70–71 % yield. The document says that by refluxing in ethanol 1,3-dipolar cycloaddition to methyl N-allyl-N-phenylcarbamate of 4-chlorophenylcarbonitrile N-oxide, generated from 4-chlorobenzaldehyde oxime under action of chloroamine Ò for 5 hours, methyl N-[3-(4-chlorophenyl)-4,5-dihydro-5-isoxazolyl]-N-phenylcarbamate is obtained. By [3+2]-cycloaddition of 2-thienylcarbonitrile N-oxide, generated at action of chloroamine T on 2-thienylcarbaldehyde oxime, to allyl- and propargyl-N-phenylcarbamate, 3,5-disubstituted isoxazoline and isoxazole are correspondingly received. The three-component reaction of propargyl-N-phenylcarbamate with acenaphthenequinone and L-proline during its 22-hour reflux in acetonitrile (in a nitrogen atmosphere) results in the formation of (2-oxo-5t,6,,7,,7,à-tetrahydro-2Í-spiro[acenaphthylene-1,3--pyrrolizine]-2--yl) methyl phenylcarbamate. The structure of new compounds is confirmed by IR, 1H, 13C NMR, mass-spectrometry methods and by analysis of the elements.

Key words: aromatic and heterocyclic carbamates,azaheterocycles,spiro-compounds,alkylation reactions,interphase catalysis,1,3-dipolar cycloaddition