Registration Number
0220U100874,
0119U000243
, R & D reports
Title
Synthesis, structure and reactivity of new N-acyl-1,4-benzoquinoneimines. New bioactive compounds and additives for technological liquids.
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Head
Avdeenko Anatoly P., Кандидат хімічних наук
Registration Date
29-01-2020
Organization
Donbass State Engineering Academy
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The object of the study is N-acyl-1,4-benzoquinoneimines. The matter of the study is the synthesis of new earlier unknown N-acyl-1,4-benzoquinimines, N-arylaminocarbonyl(carbamoyl)-1,4-benzoquinone monoimines and their derivatives, the development of simple methods for their synthesis, the determination of structure of the compounds obtained. Methods: organic synthesis, NMR 1H and 13C spectroscopy, IR spectroscopy, quantum chemical calculations, elemental analysis. Preparative synthesis techniques have been developed and new previously unknown N-arylaminocarbonyl(carbamoyl)-1,4-benzoquinone monoimines and their derivatives with various substituents in the quinoid ring have been synthesized. These compounds are both N-monoaryl-substituted ureas and the derivatives of N-arylaminocarbonyl(carbamoyl)-1,4-benzoquinone monoimines. The combination of properties of quinonimines and urea in one compound greatly extends the possibilities of synthesis of new their derivatives. That allow to obtain new derivatives based on N-carbamoyl-1,4-benzoquinone monoimines, N-(N'-phenylcarbamyl)carbamoyl-1,4-benzoquinone monoimines, 4-(4-hydroxyphenyl)-semicarbazides, 4-(4-hydroxyphenyl)-1-acetyl (benzoyl, tosyl)semicarbazides. The scientific novelty: The simple methods of synthesis of new N-acyl-1,4-benzoquinoneimines, N-arylaminocarbonyl(carbamoyl)-1,4-benzoquinone monoimines and their derivatives, have been developed; the combination of properties of two classes (quinonimines and urea) in one compound made it possible to significantly extend the bound in the synthesis of new derivatives of N-substituted-1,4-benzoquinone monoimines; it has been found that in the solutions of N-arylaminocarbonyl- and N-carbamoyl-1,4-benzoquinone monoimines the both Z,E-isomerization and retarded rotation around –NH–C(O)– bond is observed. The mechanism of Z,E-isomerization with respect to C = N bond of the quinoid ring is the inversion.
Product Description
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2020-04-02
