The Synthesis of Stable, Complex Organocesium Tetramic Acids through the Ugi Reaction and Cesium-Carbonate-Promoted Cascades.
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.
Department of Pharmacology and Toxicology, The University of Arizona, BSW Room #351, 1041 E. Lowell St., Tucson, AZ 85721 (USA).
Guillermo
G
Martinez-Ariza
Department of Pharmacology and Toxicology, The University of Arizona, BSW Room #351, 1041 E. Lowell St., Tucson, AZ 85721 (USA).
Muhammad
M
Ayaz
Department of Chemistry and Biochemistry, The University of Arizona (USA).
Sue A
SA
Roberts
Universidad Andrés Bello, Facultad de Ciencias Exactas, Ph.D. Program in Molecular Physical Chemistry, Relativistic Molecular Physics (ReMoPhys) Group, Av. República 275, Santiago 8370146 (Chile).
Walter A
WA
Rabanal-León
Universidad Andrés Bello, Facultad de Ciencias Exactas, Ph.D. Program in Molecular Physical Chemistry, Relativistic Molecular Physics (ReMoPhys) Group, Av. República 275, Santiago 8370146 (Chile).
Ramiro
R
Arratia-Pérez
Department of Pharmacology and Toxicology, The University of Arizona, BSW Room #351, 1041 E. Lowell St., Tucson, AZ 85721 (USA). hulme@pharmacy.arizona.edu.|Department of Chemistry and Biochemistry, The University of Arizona (USA). hulme@pharmacy.arizona.edu.
Christopher
C
Hulme
D002254:Carbonates / Q000737:chemistry*; D002586:Cesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000737:chemistry*; D011789:Quantum Theory
D002254:Carbonates; D009942:Organometallic Compounds; D011760:Pyrrolidinones; D002586:Cesium; C009435:tetramic acid
Dieckmann condensation; Ugi reaction; cascade reactions; multicomponent reactions; tetramic acids