The Synthesis of Stable, Complex Organocesium Tetramic Acids through the Ugi Reaction and Cesium‐Carbonate‐Promoted Cascades

Abstract

Two structurally unique organocesium carbanionic tetramic acids have been synthesized through expeditious and novel cascade reactions of strategically functionalized Ugi skeletons delivering products with two points of potential diversification. This is the first report of the use of multicomponent reactions and subsequent cascades to access complex, unprecedented organocesium architectures. Moreover, this article also highlights the first use of mild cesium carbonate as a cesium source for the construction of cesium organometallic scaffolds. Relativistic DFT calculations provide an insight into the electronic structure of the reported compounds.

Nanoparticle Based on Poly(Ionic Liquid) as an Efficient Solid Immobilization Catalyst for Aldol Reaction and Multicomponent Reaction in Water

“…Recently, l -proline was used to synthesize the heterocyclic compound such as the 2 H -benzo­[g]­pyrazolo [3,4- b ] quinoline-5,10­(4 H ,11 H )-dione derivatives and etc., the heterocyclic compounds synthesized by the multicomponent reaction are a very important class of organic compounds which were widely used in the fields of medicine, − pesticides, and other materials . First, PILC-3 was used to catalyze the simple multicomponent reaction such as the Biginelli reaction (Table ).…”

The Synthesis of Stable, Complex Organocesium Tetramic Acids through the Ugi Reaction and Cesium‐Carbonate‐Promoted Cascades

“…However,r eaction work-up was solvent evaporation, followed by column chromatography (note:n ob ase quenching step was performed). Interestingly NMR analysis revealed amissing proton in the tetramic acid ( Figure 2) and subsequent X-ray crystallography [22] confirmed the presence of an unprecedented organocesium complex 7a (see Figure 2a sw ell as Figures S1 and S2). Interestingly,b y changing the LC/MS eluent (to H 2 O/CH 3 CN,1:9), the mass of the expected tetramic acid plus the cesium atom was found to be consistent with the observed X-ray data.…”

X-Ray Crystallographic Analysis, EPR Studies, and Computational Calculations of a Cu(II) Tetramic Acid Complex

“…Additionally, more complexes of naturally derived tetramic acids have been reported, the most important being those of decylidene tetramic acid (C12-TA), a degradation product derived from 3-oxododecanoyl homoserine lactone (3-oxo-C 12 -HSL) that binds essential metals such as Fe(III) and Ga(III) ions [27]. Recently, a new synthetic methodology on tetramic acid core and subsequent organocesium carbanionic architectures has been explored [28]. Likewise, the synthesis of chelating agents containing the oxygen equivalent 3-acyltetronic acid scaffolds has been extensively studied [29].…”