Keto-Enol Tautomerism in Passerini and Ugi Adducts

The use of arylglyoxal as starting material in Passerini and Ugi reactions affords β-ketoamides. This has allowed to study keto-enol tautomerism in these systems and assess the way in which the presence of acyloxy or aminoacyl groups bound to the C2 position affects such tautomerism, and to investigate the reactivity of both the enol and carbonyl forms. In this work we also prove the versatility of the Passerini reaction, since depending on the conditions to which the corresponding adducts are subjected different products of synthetic interest can be obtained.

Miscellaneous Passerini Reaction for α-Acyloxy Carboxamide: Synthesis and Process Optimization Study

: An accelerating effect of “Phase Transfer Catalyst” as additive was exposed for the Passerini three-component reactions and the influence on the reaction rate was studied concerning direct involvement of reactant molecules. The most flexible reaction for the rapid formation of diverse “α-acyloxycarboxamides” using passerini reaction involved multicomponent reactions using miscellaneous 2-(prop-2-ynyloxy)benzaldehyde with various aromatic acid and slightly non-polar fragment i.e. 2-isocyano-2,3,3-trimethylbutane and the representative molecule was characterized with resepct to DEPT135 NMR technique.

C(sp3)–H Functionalization with Isocyanides

Isocyanide is well known for its multi-component reactions (MCR), such as Passerini reaction and Ugi reaction, with diverse molecular skeletons, high functional group compatibility, and good atom economy. With the...

The 100 Facets of the Passerini Reaction

This perspective aims at celebrating the 100th Anniversary of the discovery of the Passerini three component reaction. After being nearly neglected for many years, now this reaction has become quite...

Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction

A chiral heterogeneous catalyst derivative of (−)-4,5-dimethyl-3,6-bis(1-naphthyl)-1,2-benzenedisulfonimide is proven here to be efficient in a three-component asymmetric Passerini protocol, carried out in a deep eutectic solvent.

Four Component Passerini Polymerization of Bulky Monomers under High Shear Flow

We introduce a four component Passerini polymerization utilizing sterically bulky isocyanide monomers. Under typical Passerini conditions, bulky isocyanides do not react within standard Passerini reaction timescales (hours). We overcome this...