Králová Petra Ph.D.

Diversity-Oriented Synthesis Using Immobilized 2/4-Nitrobenzensulfonamides As The Key Intermediates

The Ph.D. thesis is focused on the diversity-oriented synthesis using immobilized 2/4-nitrobenzensulfonamides as the key intermediates to prepare single and fused nitrogenous heterocycles. The preparation of these derivatives was performed using solid-phase synthesis (SPS) that yielded the common intermediate, i.e. α-amino ketone which was further modified to final products. The general concept of SPS and its (dis)advantages are briefly discussed in Introduction of this thesis. The following subchapter introduces the previous research in the field of N-sulfonyl and N-acyl morpholine-3-carboxylic acid derivatives which has become a major inspiration for all of our projects described in this thesis. The following chapter Aims of the work provides the specific goals in more details. After that, the thesis continues as the State of the art to display shortly the general application of immobilized 2/4-nitrobenzensulfonamides and α-amino ketones to prepare diverse heterocycles. This subchapter is supplemented by our review article summarizing the polymer-supported syntheses of heterocycles bearing oxazine and thiazine scaffolds which is attached in Appendix B at the end of this thesis. Then the part of Results and discussion follows which is divided into eight subchapters according to the individual synthetic projects. In Conclusion part, all results are briefly summarized.

Solid-Phase Synthesis of Novel Morpholine/Thiomorpholine-3-Carboxylic Acid Derivatives

This diploma thesis deals with the preparation of novel morpholine/thiomorpholine-3-carboxylic acids derivatives with use of solid phase synthesis. The starting materials for the preparation of target compounds are four types of resin with acid-labile linkers, natural α-amino acids, sulfonyl chlorides, α-bromoacetophenones, carboxylic acids or their chlorides, trifluoroacetic acid and reducing agent (triethylsilane). The Theoretical section is devoted to the literature summarizing methods for the preparation of the target derivatives. In the Discussion part there are described issues concerning the preparation of the desired compounds. The Experimental section presents general procedures for the preparation and isolation of these derivatives followed by analytical data of the individual substances. The Conclusion part summarizes our results and their evaluation. In the last part, there are attached annexes of the prepared compounds.