Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi - 110 016, India.
Org Biomol Chem. 2020 Dec 28;18(48):9852-9862. doi: 10.1039/d0ob02046j. Epub 2020 Dec 9.
1,4-Diazabicyclo[2.2.2]octane (DABCO)-catalyzed [3 + 3] cycloaddition reaction of 3-alkylidene-2-oxindole and β,γ-unsaturated α-keto esters under mild reaction conditions afforded the spirocyclohexene-oxindole with excellent diastereoselectivity. The [3 + 3] annulation is found to proceed through a vinylogous Michael-aldol cascade reaction and it allows rapid access to a diverse set of highly functionalized spirocyclohexene-oxindoles. Also, a bioactivity study of the compounds on mammalian sarcoma cells has reflected cell growth inhibitory/anti-cancer properties.
1,4-二氮杂双环[2.2.2]辛烷(DABCO)催化 3-亚甲基-2-氧代吲哚和β,γ-不饱和α-酮酯在温和的反应条件下的[3+3]环加成反应，以极好的非对映选择性得到螺环己烯-氧吲哚。[3+3]环化反应被发现是通过乙烯基迈克尔-羟醛缩合级联反应进行的，它可以快速得到一系列具有高度官能化的螺环己烯-氧吲哚。此外，对化合物在哺乳动物肉瘤细胞上的生物活性研究反映了细胞生长抑制/抗癌特性。
