Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil.

摘要: We describe the one-pot synthesis of twenty polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) in 20 to 95% overall yields, as well four pharmacologically promising analogues an improved Diels-Alder/N-acylation/aromatization/SN2): two piperazine-linked 33 and 34%, couple Falipamil aza-analogues 30 35% yields. It is worth highlighting good substrate scope found, because final products are furnished with alkyl, aryl, heterocyclic substituents. The use chain-ring tautomerizable isocyanides (as key reagents for Ugi-type three component reaction) allowed rapid efficient assembly polysubstituted oxindoles, which were used situ toward complex products, conferring features like robustness, sustainability, approach this synthetic methodology.