2-Oksopirolidīna atvasinājumu sintēze

Abstract

Bakalaura darba literatūras apskats ir veltīts nervu sistēmas slimību ārstēšanā izmantojamo 2-oksopirolidīna struktūratvasinājumu iegūšanas metodēm. Kā informācijas avoti tika izmantoti: referatīvais žurnāls Chemical Abstracts, datu bāze Beilstein Crossfire, kā arī Interneta datu bāzes – PubMed., European Patent Office un Beilstein Abstracts. Atbilstoši pētījuma mērķiem, eksperimentāli tika pārbaudītas jau esošās un izstrādātas jaunas 3-fenil-4-nitrobutānskābes esteru, 3-fenil-4-oksobutānskābes amīdu, 4-fenil-5-metil-2-okso-1,3-dihidropirola, 4-fenil-5-metil-2-okso-1,5-dihidropirola, 3-fenil-4-nitro-2-butēnskābes esteru un 3-fenil-4-nitro-3-butēnskābes esteru iegūšanas metodes. Reducējot nitrogrupu 3-fenil-4-nitrobutānskābes esteros, vai hidrogenējot dubultsaiti dihidropirolos paaugstinātā spiedienā Reneja Ni katalizātora klātbūtnē, radās 4-fenil-5-alkil-2-oksopirolidīni. 3-Fenil-4-oksobutānskābes amidēšana un reducēšana paaugstinātā spiedienā veicināja to pārvēršanos par 4-fenil-5-alkil-2-oksopirolidīniem. Alkilējot 4-fenil-5-alkil-2-oksopirolidīnu ar 2-brometiķskābes etilesteri un apstrādājot radušos (4-fenil-5-alkil-2-oksopirolidīn-1-il)etiķskābes etilesterus ar amonija hidroksīdu tika iegūti (4-fenil-5-alkil-2-oksopirolidīn-1-il)acetamīdi.

The analysis of scientific literature is devoted to methods of 2-oxopyrrolidine structural analogues preparation, which are used for the treatment of nervous system deseases. Referative journal Chemical Abstracts, data base Beilstein Crossfire, the same as Interne data bases PubMed., European Patent Office and Beilstein Abstracts are used as informational sources. According to the goal of investigation there were realized experimental explorations of already existing and worked out new methods aimed at the prepartion of 3-phenyl-4-nitrobutanoic acid esters, 3-pheny-4-oxobutanoic acid amides, 4-phenyl-5-methyl-2-oxo-1,3-dihydropyrrole, 4-phenyl-5-methyl-2-oxo-1,5-dihydropyrrole, 3-phenyl-4-nitro-2-butenoic acid esters and 3-phenyl-4-nitro-3-butenoic acid esters. There was reached the formation of 4-phenyl-5-alkyl-2-oxopyrrolidine by the reduction of nitro group in 3-phenyl-4-nitrobutanoic acid esters or by hydrogenation of double bond in dihydropyrroles under inrcreased pressure in the presence of Ni Reney. 4-Phenyl-5-alkyl-2-oxopyrrolidine could by also obtained by amidation and reduction of 3-phenyl-4-oxobutanoic acid under inrcreased pressure. (4-Phenyl-5-alkyl-2-oxopyrrolidin-1-yl)acetamides were obtained by the alkylation of 4-phenyl-5-alkyl-2-oxopyrrolidine with 2-bromoacetic acid ethyl ester and the treatment of ethyl (4-phenyl-5-alkyl-2-oxopyrrolidin-1-yl)acetates with ammonium hydroxide.