112776-37-1Relevant articles and documents
Synthesis of chromeno[3,4-b]piperazines by an enol-ugi/reduction/cyclization sequence
Bornadiego, Ana,Neo, Ana G.,Marcos, Carlos F.
supporting information, (2021/05/31)
Keto piperazines and aminocoumarins are privileged building blocks for the construction of geometrically constrained peptides and therefore valuable structures in drug discovery. Combining these two heterocycles provides unique rigid polycyclic peptidomimetics with drug-like properties including many points of diversity that could be modulated to interact with different biological receptors. This work describes an efficient multicomponent approach to condensed chromenopiperazines based on the novel enol-Ugi reaction. Importantly, this strategy involves the first reported post-condensation transformation of an enol-Ugi adduct.
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
Zamudio-Medina, Angel,García-González, Ailyn N.,Herrera-Carrillo, Genesis K.,Zárate-Zárate, Daniel,Benavides-Macías, Adriana,Tamariz, Joaquín,Ibarra, Ilich A.,Islas-Jácome, Alejandro,González-Zamora, Eduardo
, (2018/04/06)
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[3,4b]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.
Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: Reaction development and mechanistic insights
Parsons, Andrew T.,Smith, Austin G.,Neel, Andrew J.,Johnson, Jeffrey S.
supporting information; experimental part, p. 9688 - 9692 (2010/09/06)
An enantioselective preparation of 2,5-cis-disubstituted pyrrolidines has been achieved via a dynamic kinetic asymmetric transformation (DyKAT) of racemic donor-acceptor cyclopropanes and (E)-aldimines. Mechanistic studies suggest that isomerization of the aldimine or resultant iminium to the Z geometry is not a pathway that furnishes the observed 2,5-cis-disubstituted products.