Chatzopoulou, M;
Martínez, RF;
Willis, NJ;
Claridge, TDW;
Wilson, FX;
Wynne, GM;
Davies, SG;
(2018)
The Dimroth rearrangement as a probable cause for structural misassignments in imidazo[1,2-a]pyrimidines: A 15N-labelling study and an easy method for the determination of regiochemistry.
Tetrahedron
, 74
(38)
pp. 5280-5288.
10.1016/j.tet.2018.06.033.
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Abstract
Structural misassignments are often seen for complex natural products, but this can also be an issue with seemingly simpler structures. In this paper, we describe how, using a15N-labelled analogue, we established that the Dimroth rearrangement can occur in imidazo[1,2-a]pyrimidines and result in an incorrect regiochemical assignment of such compounds. These studies supported a rearrangement mechanism involving addition of hydroxide ion followed by ring opening. It was also observed that C(2) and C(3) substituted regioisomers could be readily distinguished using1H NMR spectroscopy.
| Type: | Article |
|---|---|
| Title: | The Dimroth rearrangement as a probable cause for structural misassignments in imidazo[1,2-a]pyrimidines: A 15N-labelling study and an easy method for the determination of regiochemistry |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1016/j.tet.2018.06.033 |
| Publisher version: | https://doi.org/10.1016/j.tet.2018.06.033 |
| Language: | English |
| Additional information: | © 2018 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/). |
| Keywords: | Dimroth rearrangement, Imidazo[1,2-a]pyrimidine, Azaheterocycle, Polyazaindolizine, Misassignment |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Brain Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Brain Sciences > UCL Queen Square Institute of Neurology UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Brain Sciences > UCL Queen Square Institute of Neurology > Department of Neuromuscular Diseases |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10054073 |
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