Baumann Marcus, Baxendale Ian R
Department of Chemistry, University of Durham , South Road, DH1 3LE, Durham United Kingdom.
J Org Chem. 2015 Nov 6;80(21):10806-16. doi: 10.1021/acs.joc.5b01982. Epub 2015 Oct 28.
An efficient reaction cascade delivering a series of pyrrolo[1,2-a]quinolines bearing phosphonate or phosphine oxide moieties is presented. This sequence exploits the in situ transformation of propargylic alcohols into transient allenes by means of a strategic [2,3]-sigmatropic rearrangement followed by trapping of the resulting allenes by an adjacent pyrrole ring. Furthermore, the initial small scale batch process was successfully translated into a continuous flow process allowing efficient preparation of selected pyrrolo[1,2-a]quinolines on multigram scale without any safety concerns due to the reaction's inherent exothermic profile.
本文介绍了一种高效的反应串联，可生成一系列带有膦酸酯或氧化膦部分的吡咯并[1,2-a]喹啉。该反应序列利用炔丙醇通过策略性的[2,3]-σ迁移重排原位转化为瞬态丙二烯，随后相邻的吡咯环捕获生成的丙二烯。此外，最初的小规模间歇过程成功转化为连续流动过程，能够在多克规模上高效制备选定的吡咯并[1,2-a]喹啉，且由于反应固有的放热特性，不存在任何安全问题。
