Yingcharoen, Prapussorn; Natongchai, Wuttichai; Poater, Albert; D’ Elia, Valerio published an article in 2020, the title of the article was Intertwined chemistry of hydroxyl hydrogen-bond donors, epoxides and isocyanates in the organocatalytic synthesis of oxazolidinones versus isocyanurates: rational catalytic investigation and mechanistic understanding.Synthetic Route of 102-07-8 And the article contains the following content:
The use of hydroxyl hydrogen bond donors (HBDs) was investigated in cycloaddition of isocyanates to epoxides to afford 3-aryl-2-oxazolidinones I [R1 = H, 2-Me, 4-NO2, etc.; R2 = Et, CH2OCH2CH=CH2, CH2OCH2Ph, etc.] as a class of heterocycles with promising applications in pharmaceutical chem. In this work, a systematic investigation of readily available HBDs as catalytic components of binary systems for latter cycloaddition reaction was carried out. Such a study showed crucial role of HBDs’ pKa1 value in driving selectivity of reaction toward oxazolidinones as opposed to formation of oligomeric isocyanurates or ureas, with most acidic HBDs (pKa1: 3-4) displaying best catalytic performance. Mechanistic investigation with the support of DFT calculations allowed deeper insight into reaction dynamics and origin of exptl. observed chemoselectivity for cyclization vs. cyclo-oligomerization at different reaction temperatures, shedding light on a strictly intertwined chem. between the HBDs, isocyanates and epoxides. The experimental process involved the reaction of 1,3-Diphenylurea(cas: 102-07-8).Synthetic Route of 102-07-8
The Article related to aryl oxazolidinone chemoselective preparation dft reaction mechanism, isocyanate epoxide cycloaddition organocatalyst hydrogen bond donor, Heterocyclic Compounds (More Than One Hetero Atom): Oxazoles, Isoxazoles and other aspects.Synthetic Route of 102-07-8
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