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Organic Chemistry

Tutor Doc. Ing. Michal Hocek, PhD. DSc.

Michal Hocek

Topic Synthesis of substitted purines, deazapurines and related heterocycles through the combination of C-H activations and cross-coupling reactions
Faculty PřF UK

Novel C-H activation reactions (aminations, borylations, sulfenylations, phosphinylations etc.) of purines, deazapurines and some related fused heterocycles will be developed. These reactions will be utilized (in combination with C-C and/or C-X cross-coupling reactions) in the development of iterative regioselective syntheses of derivatives bearing multiple substituents. Finally, these methodologies will be applied for the synthesis of large series and libraries of derivatives for biological activity testing.

Leading references:
1. Čerňa, I.; Pohl, R.; Klepetářová, B.; Hocek, M. "Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation and Direct C-H Arylation Reactions." J. Org. Chem. 2008, 73, 9048-9054.
2. Klečka, M.; Pohl, R.; Klepetářová, B.; Hocek, M. "Direct C-H Borylation and C-H Arylation of Pyrrolo[2,3-d]pyrimidines: Synthesis of 6,8-Disubstituted 7-Deazapurines" Org. Biomol. Chem. 2009, 7, 866-868.
3. Čerňa, I.; Pohl, R.; Klepetářová, B.; Hocek, M. "Intramolecular Direct C-H Arylation Approach to Fused Purines. Synthesis of Purino[8,9-f]phenanthridines and 5,6-Dihydropurino[8,9-a]isoquinolines" J. Org. Chem. 2010, 75, 2302-2308.
4. Klečka, M.; Pohl, R.; Čejka, J.; Hocek, M. "Direct C-H sulfenylation of purines and deazapurines" Org. Biomol. Chem. 2013, 11, 5189-5193.