RESUMO
Herein a novel access to functionalizable 6-substituted imidazo[1,2-a]imidazole scaffolds is described. The reactivity of this heterobicyclic unit toward direct C-H arylation was studied, and conditions allowing regioselective arylation at position 3 were successfully developed. The practicability of this method is manifested by the ligandless conditions and low catalyst loading. The strategy is functional group tolerant and provides rapid access to a large variety of 3,6-di(hetero)arylated imidazo[1,2-a]imidazole derivatives. A second arylation at position 2 was then carried out, and a library of diversified 2,3,6-tri(hetero)arylated imidazo[1,2-a]imidazoles was generated in good yields. A one-pot, two-step procedure was finally developed.
RESUMO
Highly regioselective: An efficient synthesis of the imidazo[1,2-b]pyrazole core has been developed, and the first regioselective palladium-catalyzed direct arylation of the C-3 position is described (see scheme). Good to excellent yields were obtained for a wide range of aryl partners with electron-rich and electron-poor substituents. This methodology allows rapid access to a large variety of imidazo[1,2-b]pyrazole products and could open the way to the design of new biologically active compounds.
Assuntos
Pirazóis/química , Pirazóis/síntese química , Estrutura Molecular , Compostos Organometálicos/química , Paládio/química , EstereoisomerismoRESUMO
Protected pentofuranose, hexofuranose and hexopyranose hemiacetals were found to react efficiently with amines carrying a deactivating group (alkoxycarbonyl, tosyl or phosphoryl group) in the presence of a Lewis acid to give the corresponding, stable glycosylamines. Such glycosylamine derivatives are useful substrates for further elaboration into nitrogen-containing natural products and carbohydrate mimetics.
Assuntos
Acetais/química , Amino Açúcares/síntese químicaRESUMO
Synthesis and functionalization strategies of the imidazo[1,2-b]pyrazole core were developed giving a rapid access to three series of novel imidazo[1,2-b]pyrazole type derivatives: C-2/C-6/C-7 trisubstituted, C-2/C-3/C-6 tri(hetero)arylated and C-2/C-3/C-6/C-7 tetrasubstituted imidazo[1,2-b]pyrazoles. 39 of the synthetized products were evaluated for in vitro anticancer activity using the MTT colorimetric assay against 5 human and 1 murine cancer cell lines. Promising in vitro growth inhibitory activities were exhibited by some of the target compounds. Of the 39 evaluated products, 4 displayed an IC50 ≤ 10 µM in the 6 cell lines analyzed (compounds 4d, 4g, 9a, 11a). A structure activity relationship analysis is also reported in this paper.