Igushkina Anastasiya V, Golovanov Alexander A, Vasilyev Aleksander V
Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, 199034 Saint Petersburg, Russia.
S.P. Korshunov Research Laboratory No. 13, Department Chemical Technology and Resource Conservation, Togliatti State University, Belorusskaya ul., 14, 445667 Togliatti, Russia.
Molecules. 2022 Feb 13;27(4):1256. doi: 10.3390/molecules27041256.
Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones [ArC≡CCH=CHC(=O)Ar], with 3-oxo-3-phenylpropanenitrile (NCCHCOPh) in the presence of sodium methoxide MeONa as a base in MeOH at room temperature for 4-26 h affords polyfunctional δ-diketones as a product of regioselective Michael addition to the double carbon-carbon bond of starting enynones. The δ-diketones have been formed as mixtures of two diastereomers in a ratio of 2.5:1 in good general yields of 53-98%. A synthetic potential of the obtained δ-diketones has been demonstrated by heterocyclization with hydrazine into substututed 5,6-dihydro-4-1,2-diazepine.
在室温下，以甲醇钠（MeONa）作为碱，在甲醇中，直链共轭烯炔酮1,5 - 二芳基戊 - 2 - 烯 - 4 - 炔 - 1 - 酮[ArC≡CCH = CHC(=O)Ar]与3 - 氧代 - 3 - 苯基丙腈（NCCHCOPh）反应4 - 26小时，可得到多官能团δ - 二酮，这是起始烯炔酮的碳 - 碳双键区域选择性迈克尔加成的产物。δ - 二酮以两种非对映异构体的混合物形式形成，比例为2.5:1，总收率良好，为53 - 98%。通过与肼杂环化生成取代的5,6 - 二氢 - 4H - 1,2 - 二氮杂卓，证明了所得δ - 二酮的合成潜力。
