Research and Analytical Center for Giant Molecules and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 Japan.
Org Lett. 2010 Sep 17;12(18):4198-200. doi: 10.1021/ol1017504.
Propynal hydrazones are successfully converted to the corresponding 3-aminoacrylonitriles in the presence of copper catalysts in good to high yields. As an example, (Z)-N-(hex-2-ynylidene)morpholin-4-amine reacted in the presence of 10 mol % Cu(OAc)(2) in acetonitrile at 25 °C to afford (E)-3-morpholinohex-2-enenitrile ((E)-2 h) in 77% yield via C-N bond formation and subsequent β-elimination involving cleavage of N-N and C-H bonds.
丙炔腙在铜催化剂的存在下可以成功转化为相应的 3-氨基丙烯腈，产率好至高产率。例如，（Z）-N-（己-2-炔基）吗啉-4-胺在 25°C 下，在 10mol%的 Cu(OAc)2 在乙腈中反应，通过 C-N 键形成和随后涉及 N-N 和 C-H 键断裂的β-消除，以 77%的收率得到（E）-3-吗啉基己-2-烯腈（（E）-2h）。
