Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents
Harry R. Hudson, Ádám Tajti, Erika Bálint, Mátyás Czugler, Konstantin Karaghiosoff, György Keglevich
Abstract
A series of N-benzhydryl protected α-aminophosphonates with α-phenyl, α-(1-naphtyl), α-(9-anthryl) or α-(1-pyrenyl) substituents was synthesized by the Kabachnik–Fields condensation of diphenylmethylamine (benzhydrylamine), the corresponding aryl aldehyde and a dialkyl phosphite under MW irradiation. X-ray studies performed at low temperatures for a few of these α-aminophosphonates confirmed the presence of unusually short intramolecular Cα–Hδ+ ··· δ+H–Cperi contacts.
Topics & Concepts
ChemistryIntramolecular forceArylSteric effectsMicrowave irradiationAldehydeCondensationMedicinal chemistryCondensation reactionOrganic chemistryPhotochemistryCatalysisAlkylPhysicsThermodynamicsOrganophosphorus compounds synthesisSynthesis and Reactivity of Sulfur-Containing CompoundsSynthesis and Characterization of Heterocyclic Compounds