Derivati izoindolina, sinteza i biološka aktivnost. I. Prirodni i sintetski derivati izoindolina

Karminski‐Zamola, Grace

doi:10.15255/kui.2013.004

Cited by 2 publications

(1 citation statement)

References 26 publications

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“…It is worthy to note that in the same work, Falipamil ( 1 ) and various related analogues, such as the product 3 (Figure 1), were synthesized successfully via a stepwise (multistep) strategy. Indeed, almost all reports describing the synthesis of isoindolin-1-ones and pyrrolo[3,4- b ]pyridin-5-ones, including those piperazine-linked to other heterocyclic systems, have been synthesized using stepwise methodologies [8]. …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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

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Section: Introductionmentioning

confidence: 99%