B. Baumann
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 | Mar 28, 2024 |
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 |
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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.joc.5b01982.
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