СИНТЕЗ ХИНАЗОЛИНО[3,2-C][2,3]БЕНЗОДИАЗЕПИН-14(6H)-ОНОВ ОКИСЛЕНИЕМ CH-NH-СВЯЗИ В 11,12-ДИГИДРОПРОИЗВОДНЫХ
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| Title |
СИНТЕЗ ХИНАЗОЛИНО[3,2-C][2,3]БЕНЗОДИАЗЕПИН-14(6H)-ОНОВ ОКИСЛЕНИЕМ CH-NH-СВЯЗИ В 11,12-ДИГИДРОПРОИЗВОДНЫХ
SYNTHESIS OF QUINAZOLINO[3,2-C][2,3]BENZODIAZEPIN-14(6H)-ONES BY THE OXIDATION OF CH-NH-BOND IN THE 11,12-DIHYDRODERIVATIVES |
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| Creator |
Толкунов, Андрей Сергеевич
Богза, Сергей Леонидович |
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| Subject |
11,12-дигидрохиназолино[3,2-c][2,3]бензодиазепин-14(6H)-оны
хиназолино[3,2-c][2,3]бензодиазепин-14(6H)-оны окисление перманганат калия хромовый ангидрид 11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-ones quinazolino[3,2-c][2,3]benzodiazepin-14(6H)-one oxidation potassium permanganate chromic anhydride |
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| Description |
Изучена реакция окисления 11,12-дигидрохиназолино[3,2-c][2,3]бензодиазепин-14(6H)-онов с использованием перманганата калия или раствора хромового ангидрида в уксусной кислоте.
2,3-Benzodiazepines and their condensed derivatives are actively investigated in connection with the discovery of their high psychotropic activity. Recently, we proposed a method for obtaining of previously unknown 11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-ones. The 11,12 dihydroquinazolino[3,2-c][2,3]¬benzodiazepin-14(6H)-ones, obtained by Pictet-Spengler reaction of 3-amino-2-(3,4-dimetoxybenzyl)quinazoline-4(3Н)-оne with aliphatic or aromatic aldehydes, were converted to the quinazolino[3,2-c][2,3]benzodiazepin-14(6H)-ones by oxidation. The reaction of oxidation of 11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-ones with various oxidants was investigated. Potassium permanganate in methylene chloride in the presence of catalytic amounts of 18-crown-6, and chromic anhydride in acetic acid were used as the oxidants. The reaction of 11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-one with potassium permanganate gave quinazolino[3,2-c][2,3]benzodiazepin-14(6H)-one with 50 % yield. But 11-substituted 11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-ones gave corresponding products of oxidation with low yields and reaction proceeds incompletely. Reaction of 11-substituted dihydrodiazepines with chromic anhydride in 50-70 % acetic acid gave corresponding diazepines with moderate yield (30-50 %). The best yields of desired products were reached at the temperature not above 30 ºС. At the temperature above 30 ºС, the further oxidation occurs with the destruction of the diazepine cycle and yields of products are reduced. 7,12-Dihydro-thieno[2',3':4,5]pyrimido[1,2 с][2,3]benzodiazepin-14(6H)-ones react similarly. Structures of the synthesized compounds were confirmed by 1H and 13C NMR and mass spectra. |
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| Date |
2013-04-13T13:22:30Z
2013-04-13T13:22:30Z 2013 |
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| Type |
Article
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| Identifier |
2074-6652
УДК 547.856’89 http://ea.donntu.edu.ua/handle/123456789/18468 |
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| Relation |
Наукові праці ДонНТУ;Серія: Хімія і хімічна технологія, 2013. - Вип.2(21). - С.103-108
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| Publisher |
Донецк, ДонНТУ
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