Samara State Technical University, 443100 Samara, Russian Federation.
J Org Chem. 2021 Jun 4;86(11):7460-7476. doi: 10.1021/acs.joc.1c00423. Epub 2021 May 20.
A library of -4,5-dihydrofuran-3-carbonitriles was synthesized in a diastereoselective manner in good yields by the three-component reaction of β-ketonitriles, carbonyl- and semistabilized pyridinium ylide precursors, and aldehydes in the presence of piperidine. This one-pot transformation generates two C-C and one C-O bond and proceeds through a cascade Knoevenagel condensation, a Michael addition, and intramolecular S2 cyclization. Formation of cyclopropanecarbonitrile derivatives, which in some cases were obtained as major products, was found to be a competing reaction. The use of arylglyoxals changes regioselectivity and leads to 2-hydroxy-2-pyran-5-carbonitriles.
以β-酮腈、羰基和半稳定吡啶鎓叶立德前体以及醛为原料，哌啶存在下，通过三组分反应以非对映选择性方式合成了-4,5-二氢呋喃-3-甲腈库，产率良好。该一锅转化生成两个 C-C 和一个 C-O 键，并通过 Knoevenagel 缩合、迈克尔加成和分子内 S2 环化进行。发现形成环丙甲腈衍生物是一个竞争反应，在某些情况下，这些衍生物是主要产物。使用芳基乙二醛会改变区域选择性，并导致 2-羟基-2-吡喃-5-甲腈。
