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© 2018 The Authors 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.

Original publication

DOI

10.1016/j.tet.2018.06.033

Type

Journal article

Journal

Tetrahedron

Publication Date

20/09/2018

Volume

74

Pages

5280 - 5288