Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany.
J Org Chem. 2013 Jul 5;78(13):6670-6. doi: 10.1021/jo400992n. Epub 2013 Jun 14.
Indolizines carrying various substituents in positions 5-8 were obtained from readily available 2-(1H-pyrrol-1-yl)nitriles and α,β-unsaturated ketones or aldehydes in a one-pot procedure. Michael addition of the deprotonated aminonitriles to the acceptors followed by acid-catalyzed electrophilic cyclization produces 5,6-dihydroindolizine-5-carbonitriles. From these stable intermediates, substituted indolizines were obtained via base-induced dehydrocyanation.
从易得的 2-(1H-吡咯-1-基)腈和α,β-不饱和酮或醛出发，一锅法得到了在 5-8 位带有各种取代基的吲唑。去质子化的氨基腈对受体进行迈克尔加成，然后酸催化进行亲电环化，生成 5,6-二氢吲唑-5-甲腈。从这些稳定的中间体出发，通过碱诱导脱氰基得到取代的吲唑。
