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Title: | Combinatorial synthesis of derivatives of bioactive compounds via a sulfone scaffold | Authors: | GAO YONGNIAN | Keywords: | sulfone, solid-phase synthesis, triazoles, pyrroles, polymer-supported reagent, Davis reagent | Issue Date: | 8-Jan-2009 | Citation: | GAO YONGNIAN (2009-01-08). Combinatorial synthesis of derivatives of bioactive compounds via a sulfone scaffold. ScholarBank@NUS Repository. | Abstract: | This thesis focuses on combinatorial synthesis of derivatives of bioactive compounds via a sulfone scaffold.Project 1 is to extend the application of polymer-supported sodium benzenesulfinate in solid-phase synthesis. An efficient traceless solid-phase synthesis of trisubstituted and disubstituted 1,2,3-triazoles has been developed. 23 different compounds were obtained by [3+2] cycloaddition of the polymer-supported vinyl sulfones and sodium azide in good yield.Project 2 is to develop combinatorial synthesis of triazolo[4,5-b]pyridin-5-ones and pyrrolo[3,4-b]pyridin-2-ones. 22 triazolo[4,5-b]pyridin-5-ones and 10 pyrrolo[3,4-b]pyridin-2-ones were prepared by [3+2] cycloaddition of heterocyclic vinyl sulfones and azides or isocyanides in good yield and regioselectivity.Project 3 aims to develop soluble polymer-supported Davis reagent and its application in organic synthesis. An efficient synthetic route of synthesizing polymer-supported Davis reagent was devised. The reagent was successfully applied in the oxidation of the sulfides, amines, selenides, phosphines and enolates as well as the rearrangement of the imidazoles. | URI: | https://scholarbank.nus.edu.sg/handle/10635/16615 |
Appears in Collections: | Ph.D Theses (Open) |
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