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National Repository of Grey Literature 2 records found  Search took 0.01 seconds. 
New C-H activations and cross-coupling reactions for modification of deazapurine nucleobases
 Sabat, Nazarii ; Hocek, Michal (advisor) ; Tobrman, Tomáš (referee) ; Hlaváč, Jan (referee)
This PhD thesis reports the development of novel C-H activation strategies and aqueous-phase Suzuki-Miyaura cross-coupling reactions for the synthesis of modified deazapurine nucleobases. The methodologies of chemo- and regioselective synthesis of highly functionalized deazapurines have been developed by using modern C-H activation chemistry. Various functional groups such as amino-, imido-, silyl- and phosphonyl- were introduced by C-H activation reactions. Amino deazapurine derivatives were synthesized by developed Pd/Cu-catalyzed direct C-H amination and C-H chloroamination of 6-substituted 7-deazapurines with N-chloro-N- alkyl-arylsulfonamides. C-H imidation reactions of pyrrolopirimidines were performed under ferrocene catalysis with N-succinimido- or N-phtalimidoperesters. In order to obtain silylated derivatives, Ir-catalyzed C-H silylations of phenyldeazapurines with alkyl silanes were designed. Highly interesting deazapurine phosphonates were prepared by using Mn-promoted C-H phosphonation method and were further transformed into the corresponding phosphonic acids. All of the developed direct C-H functionalization reactions proceeded regioselectively at position 8 in deazapurine core, except for C-H silylation where reaction undergoes mainly as directed ortho C-H silylation on phenyl ring,...
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Synthesis of novel C-nucleosides with modified sugar
 Havlíček, Vojtěch ; Hocek, Michal (advisor) ; Janeba, Zlatko (referee)
In this bachelor thesis, a new method of preparation of C-nukleosides with 2'-deoxy-2',2'-difluoro modified sugar part was developed. During the research, nucleophilic addition on furanolacton was used and for this modification, the method of modular approach was developed. Using this method, it is possible to prepare a series of structurally similar compounds. We succeeded in preparing two C-nukleosides, potentially biologically active substances.
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