Jaunu C-C saišu veidošana aziridīn-2-karbonskābes atvasinājumos, saglabājot trīslocekļu slāpekļa heterociklus
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Latvijas Universitāte
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lav
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ANOTĀCIJA. Jaunu C-C saišu veidošana aziridīn-2-karbonskābes atvasinājumos,
saglabājot trīslocekļu slāpekļa heterociklus. Štrumfs B., zinātniskais vadītājs Dr.
ķīm. Trapencieris P. Promocijas darbs, 165 lappuses, 6 attēli, 3 tabulas, 100 literatūras
avoti. Latviešu valodā.
AZIRIDĪNI, AZIRIDĪN-2-KARBONSKĀBE, KARBANJONI, ENOLĀTI,
DEPROTONĒŠANA, ANJONU ALKILĒŠANA, LITIJORGANISKIE REAĢENTI,
STIPRĀS BĀZES, ELEKTROFĪLĀS REAKCIJAS, ACILGRUPU MIGRĀCIJA
Darbā pētītas aziridīnu karbanjonu īpašības un aziridīnu anjonu metodoloģijas
pielietojums aziridīn-2-karbonskābes atvasinājumu sintēzē. Iegūta virkne
funkcionalizētu aziridīn-2-karbonskābes atvasinājumu. Parādīta diaziridinilketonu un
aziridīn-2,2-dikarbonskābes esteru veidošanās kondensācijas un acilgrupas 1-2
migrācijas reakcijās. Iegūti C(2) alkilēti aziridīn-2-karbonskābes esteri un amīdi.
Pirmo reizi iegūti un alkilēti stabilizēti 1-N,N-dialkilkarbamoilaziridīn-2-
karbonskābes esteru anjoni.
ANNOTATION. Formation of new C-C bonds in the derivatives of aziridine-2-carboxylic acid with retention of aziridine ring. Štrumfs B., supervisor Dr. chem. Trapencieris P. PhD thesis, 165 pages, 6 figures, 3 tables, 100 literature references. In Latvian. AZIRIDINE, AZIRIDINE-2-CARBOXYLIC ACID, CARBANIONS, ENOLATES, DEPROTONATION, ANION ALKYLATION, ORGANOLITHIUM REAGENTS, STRONG BASES, ELECTROPHILIC REACTIONS, ACYL GROUP MIGRATION In this thesis properties of aziridine carbanions and application of aziridine anion methodology for the synthesis of derivatives of aziridine-2-carboxylic acid were studied. A series of functional derivatives of aziridine-2-carboxylic acid were obtained. Formation of diaziridinyl ketones and esters of aziridine-2,2-dicarboxylic acid in the intermolecular condensation reactions and intramolecular acyl 1-2 migration was shown. C(2) Alkylated aziridine-2-carboxylic esters and amides were obtained. For the first time stabilized aziridinyl anions of 1-N,Ndialkylcarbamoylaziridine- 2-carboxylates were obtained and successfully alkylated.
ANNOTATION. Formation of new C-C bonds in the derivatives of aziridine-2-carboxylic acid with retention of aziridine ring. Štrumfs B., supervisor Dr. chem. Trapencieris P. PhD thesis, 165 pages, 6 figures, 3 tables, 100 literature references. In Latvian. AZIRIDINE, AZIRIDINE-2-CARBOXYLIC ACID, CARBANIONS, ENOLATES, DEPROTONATION, ANION ALKYLATION, ORGANOLITHIUM REAGENTS, STRONG BASES, ELECTROPHILIC REACTIONS, ACYL GROUP MIGRATION In this thesis properties of aziridine carbanions and application of aziridine anion methodology for the synthesis of derivatives of aziridine-2-carboxylic acid were studied. A series of functional derivatives of aziridine-2-carboxylic acid were obtained. Formation of diaziridinyl ketones and esters of aziridine-2,2-dicarboxylic acid in the intermolecular condensation reactions and intramolecular acyl 1-2 migration was shown. C(2) Alkylated aziridine-2-carboxylic esters and amides were obtained. For the first time stabilized aziridinyl anions of 1-N,Ndialkylcarbamoylaziridine- 2-carboxylates were obtained and successfully alkylated.