Phosphorylthioureas and phosphorylureas containing amino acid fragments

Synthesis and Evaluation of N-Diaminophosphoryl Aminothioureas as Bifunctional Catalysts for Vinylogous Aldol Reactions of Isatins and 2(3H)-Furanones

“…Our studies began with the synthesis of N -diaminophosphoryl aminothioureas 4 , the potential catalysts for the vinylogous aldol reaction. The general strategy for their preparation involved the synthesis of a series of chiral diamine-derived diaminophosphoryl chlorides 6 (Figure ) and their conversion to the isothiocyanate derivatives 7 by adaptation of reported methods for related compounds . Subsequent reaction of 7 with selected diamines 8 provided 4 (65–88% yield over three steps for 4a – 4n , and 91% yield over two steps, from the commercially available diaminophosphoryl chloride, for 4o ).…”

“…The general strategy for their preparation involved the synthesis of a series of chiral diamine-derived diaminophosphoryl chlorides 6 ( Figure 2 ) and their conversion to the isothiocyanate derivatives 7 by adaptation of reported methods for related compounds. 16 Subsequent reaction of 7 with selected diamines 8 provided 4 (65–88% yield over three steps for 4a – 4n , and 91% yield over two steps, from the commercially available diaminophosphoryl chloride, for 4o ). This strategy and the catalysts 4 prepared for this study are shown in Figure 3 .…”

3,5‐Bis(arylidene)piperid‐4‐ones Containing 1,3,2‐Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity

“…In the other approach, the desired compounds, the main skeleton of which was connected with the oxazaphosphorinane moiety via a thiocarbamoyl linker, were readily obtained by the reaction of NH ‐precursors 1a–c with isothiocyanate 3 derived, in turn, from the chloride 2 according to the known procedure . The reaction proceeds smoothly in CHCl 3 at room temperature to give the crude thioureas 5a–c in high yields.…”

“…IR spectra were recorded in KBr pellets on a Magna‐IR750 (Nicolet, Madison, WI) Fourier spectrometer, resolution 2 cm −1 , 128 scans. The starting 3,5‐bis(arylidene)piperid‐4‐ones 1a–e and compounds 2 and 3 were prepared according to the known procedures, and their chemical–physical characteristics fit well with the literature data. All reagents and solvents used were obtained from Aldrich (St. Louis, MO) and used without further purification.…”