A number of chiral racemic and enanthiopure thiophosphorylated thioureas were synthesized by the reaction of 2‐aminobutan‐1‐ol and 1‐(a‐aminobenzyl)‐2‐naphthol with O,O‐diethyl thiophosphoryl isothiocyanate. It was found that such thioureas undergo the cyclization reaction under basic conditions with hydrogen sulfide elimination and the formation of thiophosphorylated oxasines. X‐Ray single crystal diffraction revealed that the structure of thiourea is close to the prereaction state of the cyclization reaction.
A new diastereoselective synthesis of α-aminophosphonates has been developed, based on the reaction of trialkyl phosphites with a chiral imines, derived from (R)-or (S)-1-(α-aminobenzyl)-2-naphthol, in the presence of trifluoroacetic acid. The major diastereomer of obtained aminophosphonates can be separated by crystallization from an appropriate solvent. The desired α-aminophosphonic acids can be obtained in enantiopure form by treating the corresponding diastereomers with HCl.
The series of tautomeric 1,3‐diarylnaphthoxazines (the Betti base precursors) was obtained by the interaction of 2‐naphthols and 1,3,5‐trisaryl‐2,4‐diazapenta‐1,4‐dienes. Their structure has been established in solid state and solution.
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