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

Baumann, B.; Baxendale, I.R.

Abstract

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.

Citation

Baumann, B., & Baxendale, I. (2015). Batch and Flow Synthesis of Pyrrolo[1,2-a]-quinolines via an Allene-Based Reaction Cascade. Journal of Organic Chemistry, 80(21), 10806-10816. https://doi.org/10.1021/acs.joc.5b01982

• Journal Article Type: Article
• Acceptance Date: Oct 19, 2015
• Publication Date: Nov 6, 2015
• Deposit Date: Oct 24, 2015
• Publicly Available Date: Oct 19, 2016
• Journal: Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 80
• Issue: 21
• Pages: 10806-10816
• DOI: https://doi.org/10.1021/acs.joc.5b01982
• Public URL: https://durham-repository.worktribe.com/output/1419386