Batch and Flow Synthesis of Pyrrolo[1,2-a]-quinolines via an Allene-Based Reaction Cascade

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• 作者：Marcus Baumann ; Ian R. Baxendale
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：80
• 期：21
• 页码：10806-10816
• 全文大小：476K
• ISSN：1520-6904

文摘

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鈥檚 inherent exothermic profile.