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DOI: 10.1039/A900748B (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 1333-1338

A Dimroth rearrangement of pyrimidine nucleosides

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David Loakes, Daniel M. Brown and Stephen A. Salisbury

Abstract

N[hair space] 4-Acylamino-2′-deoxycytidine derivatives, 4a–c, undergo acid-promoted cyclisation to give [1,2,4]triazolo[4,3-c]pyrimidin-5(6H)-ones, 5a–c, in the presence of pyridinium chloride. This reaction has been demonstrated for a series of analogues. Treatment of the cyclised products in basic media gives rise to a novel Dimroth-type rearrangement leading to [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones, 7a–c. The crystal structure of one such product, 15, was confirmed by X-ray analysis.

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