| Title |
1,2-oksazetidinų ir 1,5,2,6-ditiadiazokanų taikymas N,O — ir N,S — heterociklų sintezėje / |
| Translation of Title |
Application of 1,2-oxazetidines and 1,5,2,6-dithiadiazocanes in the synthesis of various N,O— and N,S— heterocycles. |
| Authors |
Javorskis, Tomas |
| Full Text |
|
| Pages |
24 |
| Keywords [eng] |
1,2-oxazetidine ; 1,5,2,6-dithiadiazocane ; electrophilic reagents ; organometallic |
| Abstract [eng] |
The main aim of this research was to synthesize electrophilic oxygen and sulfur atom containing reagents, investigate their stability, reactivity and potential applications. New 1,2-oxazetidine derivatives were synthesized as four-membered oxaziridine analogues that embody selective electrophilic oxygen reactivity in reactions with various nucleophiles, allowing to form valuable phenol derivatives with nitrogen terminated two-carbon-atom tether. Synthetic versatility of these products led to efficient synthesis of six-, seven- and eight-membered heterocyclic systems. Further studies include the introduction of newly developed scalable method for the synthesis of thiazetidine dimer–1,5,2,6-dithiadiazocane and its enantiopure derivatives, using key S-N bond retrosynthetic disconnection. High reactivity of electrophilic sulfur reagent towards nucleophiles allowed straightforward synthesis of various benzothiomorpholines. In similar manner, seven- or eight-membered heterocycles were synthesized. The last chapter of this thesis is dedicated to chemoselective sulfonamide deprotection. New deprotection method under near stoichiometric acidic conditions was extended beyond simple deprotection to [2+2+2] cyclization reactions of ynamides and nitriles and intra- and intermolecular sulfonylation of electron-rich substrates. |
| Dissertation Institution |
Vilniaus universitetas. |
| Type |
Summaries of doctoral thesis |
| Language |
Lithuanian |
| Publication date |
2018 |
