Dihydropyrrolo[1,2-b]pyrazoles: withasomnine and related compounds

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Publikace nespadá pod Ekonomicko-správní fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.
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GALETA Juraj TENORA Lukáš MAN Stanislav POTÁČEK Milan

Rok publikování 2013
Druh Článek v odborném periodiku
Časopis / Zdroj Tetrahedron
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www http://www.sciencedirect.com/science/article/pii/S0040402013009277
Doi http://dx.doi.org/10.1016/j.tet.2013.06.009
Obor Organická chemie
Klíčová slova allenyl azine; withasomnine; cycloaddition; dihydropyrrolo[1.2-b]pyrazole; Kulinkovich
Popis In the paper we indicate the increasing importance of derivatives containing a dihydropyrrolo[1,2-b]pyrazole (DPP) core. We try to show our synthetic approach based on an improved Kulinkovich method as well as our new synthetic pathway. A complex methodology involving the preparation of substituted DPPs focuses on withasomnine and the synthesis of several structurally related compounds. The developed reaction protocols enable the preparation of the mentioned bicyclic system with broadly diverse substitution. Thus, we are able to prepare systems with aliphatic, aromatic, polyaromatic, heteroaromatic, TMS, and even adamantane substitution with known biologically active properties. The reaction protocol, consisting of two multi-step synthetic pathways, includes Sonogashira and Suzuki-Miyaura cross-coupling reactions, allenyl synthon formation, Kulinkovich cyclopropanation, ring transformations, and nonsymmetrical homoallenyl azines cycloadditions. Moreover, we prepared compounds with a resemblance to other bioactive species: fadrozole, nagstatine, an antitumor agent LY2109761 and a mixed lineage kinase 7 inhibitor DHP-2.
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