A.E. Favorsky Irkutsk Institute of Chemistry SB RAS, 1 Favorsky St, Irkutsk, 664033, Russian Federation.
Org Biomol Chem. 2021 Mar 28;19(12):2703-2715. doi: 10.1039/d1ob00193k. Epub 2021 Mar 5.
A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridines via t-BuOK/DMSO-promoted C-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of the in situ generated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available starting materials and the absence of transition-metal catalysts, oxidants and undesirable byproducts. A wide synthetic utility of the developed approach was demonstrated by the synthesis of trisubstituted, tetrasubstituted and fused pyridines.
一种新颖的一锅两步法，通过 t-BuOK/DMSO 促进各种甲基酮与缺电子炔烃（炔酮）的 C-乙烯基化，然后用醋酸铵使原位生成的不饱和 1,5-二羰基物种环化，合成 2,4,6-三芳基吡啶。该方法具有高区域选择性、可用的起始原料以及无过渡金属催化剂、氧化剂和不需要的副产物等竞争优势。所开发方法的广泛合成实用性通过合成三取代、四取代和稠合吡啶得到了证明。
