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 |
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| Authors: | Maria Chatzopoulou R. Fernando Martínez Nicky J. Willis Timothy D.W. Claridge Francis X. Wilson Graham M. Wynne Stephen G. Davies Angela J. Russell |
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| Affiliation: | 1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK;2. Summit Therapeutics plc, 136a Eastern Avenue, Milton Park, Abingdon, Oxfordshire, OX14 4SB, UK;3. Department of Pharmacology, University of Oxford, Mansfield Road, Oxford, OX1 3PQ, UK |
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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 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. |
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| Keywords: | Dimroth rearrangement Azaheterocycle Polyazaindolizine Misassignment |
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