Okuda, Y., Seo, T., Shigezane, Y., Watanabe, H., Akashi, H., Iwanaga, T. and Orita, A.
A facile and versatile synthesis of phosphoryl ynamines I [Ar1 = C6H5, 4-OMeC6H4; Ar2 = C6H5, 4-MeC6H4, 2-naphthyl, etc.] via C(sp)-N bond formation was established. An electron-withdrawing phosphoryl group was installed onto the ynamines to isolate them by column chromatog. Phosphoryl ynamines were synthesized by treatment of bromo(phosphoryl)ethyne with diarylamine in the presence of K3PO4. Single-crystal X-ray anal. indicated double-bond characters of N-C, C≡C, and C-P bonds in the N-CC-P moiety. Phosphoryl ynamines I [Ar1 = C6H5; Ar2 = C6H5, 4-MeC6H4, 4-OMeC6H4] could be used as terminal ynamine precursors in dephosphorylation/copper-catalyzed click reaction to form the corresponding 4-amino-1,2,3-triazoles II [R = n-decyl, C6H5, 4-OMeC6H4, etc.] in moderate yields.
Research papers (academic journals)
