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

Baumann, B.; Baxendale, I.R.

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


Authors

B. Baumann



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

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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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