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Title: Combinatorial synthesis of derivatives of bioactive compounds via a sulfone scaffold
Keywords: sulfone, solid-phase synthesis, triazoles, pyrroles, polymer-supported reagent, Davis reagent
Issue Date: 8-Jan-2009
Source: 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.
Appears in Collections:Ph.D Theses (Open)

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