Journal article

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

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 a 15N-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 using 1H NMR spectroscopy.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Chatzopoulou, M., Martínez, R., Willis, N., Claridge, T., Wilson, F., Wynne, G., Davies, S., & Russell, A. (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), 5280–5288.

MLA Style

Chatzopoulou, M, et al. “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, vol. 74, no. 38, 2018, pp. 5280–88.

Chicago Style

Chatzopoulou, M, R Martínez, N Willis, et al. 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): 5280–88.
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Files:: Chatzopoulou-et-al-2018-Tetrahedron.pdf

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Publisher copy:: 10.1016/j.tet.2018.06.033

Authors

+ Chatzopoulou, M More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author
ORCID:: 0000-0003-1886-7705

+ Martínez, R More by this author

Role:: Author

+ Willis, N More by this author

Role:: Author

+ Claridge, T More by this author

Institution:: University of Oxford
Division:: MPLS Division
Department:: Chemistry
Role:: Author
ORCID:: 0000-0001-5583-6460

+ Wilson, F More by this author

Role:: Author

More authors...

+ Duchenne UK More from this funder

+ Summit Therapeutics plc More from this funder

Publisher:: Elsevier
Journal:: Tetrahedron More from this journal
Volume:: 74
Issue:: 38
Pages:: 5280-5288
Publication date:: 2018-06-21
Acceptance date:: 2018-06-14
DOI:: 10.1016/j.tet.2018.06.033
ISSN:: 0040-4020

Keywords:: azaheterocycle

polyazaindolizine

Dimroth rearrangement

misassignment

imidazo[1,2-a]pyrimidine
Pubs id:: pubs:889206
UUID:: uuid:868e34b9-d8a7-4374-bb3e-73547b0e1783
Local pid:: pubs:889206
Source identifiers:: 889206
Deposit date:: 2018-08-30
ARK identifier:: ark:/29072/ora_868e34b9d8a74374bb3e73547b0e1783

Terms of use

Copyright holder:: Chatzopoulou et al
Copyright date:: 2018
Notes:: Copyright © 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/).

Licence:: CC Attribution (CC BY)

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