Chiral Thiophosphorylated Thioureas: Synthesis, Structure, and Cyclization Reaction

Abstract

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.

Recent advances in the transformation reactions of the Betti base derivatives

“…Further, a number of chiral racemic and enanthiopure thiophosphorylated thioureas 58 synthesized by the reaction of 1-(α-aminobenzyl)-2-naphthol 1 with O , O -diethyl thiophosphoryl isothiocyanate 59 in dry benzene at room temperature for 24 h. It was found that such thioureas undergo the cyclization reaction under basic conditions with hydrogen sulfide elimination via two methods (method A: in dry acetone, triethylamine or 4-(dimethylamino)pyridine at room temperature for 7 days; method B: in chloroform and hexane, N , N ′-dicyclohexylcarbodiimide at reflux for 4 h) and afforded thiophosphorylated oxasines 60 as depicted in Scheme 19. 44…”