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
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...
| Những tác giả chính: | , , , , , , , |
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| Định dạng: | Journal article |
| Được phát hành: |
Elsevier
2018
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| _version_ | 1826282946623963136 |
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| author | Chatzopoulou, M Martínez, R Willis, N Claridge, T Wilson, F Wynne, G Davies, S Russell, A |
| author_facet | Chatzopoulou, M Martínez, R Willis, N Claridge, T Wilson, F Wynne, G Davies, S Russell, A |
| author_sort | Chatzopoulou, M |
| collection | OXFORD |
| description | 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. |
| first_indexed | 2024-03-07T00:51:30Z |
| format | Journal article |
| id | oxford-uuid:868e34b9-d8a7-4374-bb3e-73547b0e1783 |
| institution | University of Oxford |
| last_indexed | 2024-03-07T00:51:30Z |
| publishDate | 2018 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | oxford-uuid:868e34b9-d8a7-4374-bb3e-73547b0e17832022-03-26T22:04:49ZThe 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 regiochemistryJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:868e34b9-d8a7-4374-bb3e-73547b0e1783Symplectic Elements at OxfordElsevier2018Chatzopoulou, MMartínez, RWillis, NClaridge, TWilson, FWynne, GDavies, SRussell, AStructural 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. |
| spellingShingle | Chatzopoulou, M Martínez, R Willis, N Claridge, T Wilson, F Wynne, G Davies, S Russell, A 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 |
| 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
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