The application of "click chemistry" for the decoration of 2(1H)-pyrazinone scaffold: generation of templates.
The "click chemistry" approach has been explored on the 2-(1H)-pyrazinone scaffold for the generation of pharmacologically interesting heterocyclic moieties. Huisgen 1,3-dipolar cycloaddition has been evaluated as the key step for the construction of the 1,2,3-triazole ring at the C-3 position of 2-(1H)-pyrazinones. Two different pathways have been successfully evaluated: (1) via C-C or C-O linkage of the acetylenic part to the C-3 position of the 2-(1H)-pyrazinone scaffold or (2) via azide introduction in the C-3 position. The subsequent application of "click chemistry" resulted in the formation of hitherto unknown skeletons. Microwave irradiation has successfully been applied in different steps of the sequence.
Kaval
Nadya
N
Laboratory for Organic Synthesis, University of Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.
Ermolat'ev
Denis
D
Appukkuttan
Prasad
P
Dehaen
Wim
W
Kappe
C Oliver
CO
Van der Eycken
Erik
E
D000114:Acetylene / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D020650:Combinatorial Chemistry Techniques; D006571:Heterocyclic Compounds / Q000737:chemistry / Q000494:pharmacology; D008872:Microwaves; D008956:Models, Chemical; D015394:Molecular Structure; D011719:Pyrazines / Q000138:chemical synthesis* / Q000494:pharmacology
D001386:Azides; D006571:Heterocyclic Compounds; D011719:Pyrazines; D000114:Acetylene