Construction of Highly Functionalized Piperazinones via Post-Ugi Cyclization and Diastereoselective Nucleophilic Addition

Abstract

A novel method for the generation of uniquely functionalized piperazinones by utilizing post-Ugi functionalization is described. The method involves an Ugi reaction with aminoacetaldehyde dimethyl acetal, followed by acid-mediated cyclization to generate the iminium precursor that was subjected to nucleophilic addition in a diastereoselective manner. The method was also employed to synthesize trans-dragmacidine C and praziquantel-like molecules.

Six‐Component Reactions and Beyond: The Nuts and Bolts

“…[34,35] Recent developments exemplify the versatility of the Ugi-adduct, describing the preparation high utility scaffolds via metal-mediated or metalfree post-Ugi transformations. [36][37][38][39][40][41][42][43] In addition to the Ugi reaction, a battery of MCRs are available in the tool box of the modern day chemist namely Petasis, Povarov and Groebke-Blackburn-Bienaymé reactions to name but a few. [44][45][46] Indeed, it must be noted that the discovery of each new MCR often spawns efforts from prominent chemists drawn on these named reactions to shorten and create a novel synthetic routes.…”

“…Moreover, the Ugi‐4CR has influenced a growing body of research in material sciences and chemical biology [34,35] . Recent developments exemplify the versatility of the Ugi‐adduct, describing the preparation high utility scaffolds via metal‐mediated or metal‐free post‐Ugi transformations [36–43] . In addition to the Ugi reaction, a battery of MCRs are available in the tool box of the modern day chemist namely Petasis, Povarov and Groebke‐Blackburn‐Bienaymé reactions to name but a few [44–46] .…”

Discovery of 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one derivatives as possible antileishmanial agents

“…2). 27 Inspired by previous reports and in continuation of our ongoing efforts to identify medicinally important structural frameworks, [28][29][30][31][32][33][34][35][36] a series of N-alkylated pyrroloquinolinone derivatives were designed and synthesized, and their antileishmanial efficacy was evaluated against visceral leishmaniasis (VL).…”

Advances in Base‐Mediated Post‐Ugi Transformations via Peptidyl Anion Trapping

“…Our research group is actively engaged in exploring novel post-Ugi transformations [21][22][23][24][25] and recently, we have been working on base-mediated post-Ugi transformations to access novel bioactive compounds for drug discovery. [26][27][28][29] Encouraged by our findings and related research worldwide, we present an exciting review highlighting the base-mediated post-Ugi transformations by trapping the peptidyl anion.…”