Regioselective synthesis of the 3,4-dihydrofuro[3,2-d]pyrimidin-2(1H)-one skeleton: a new class of compound

Koza G., Ozcan S., ŞAHİN E., BALCI M.

TETRAHEDRON, vol.65, no.31, pp.5973-5976, 2009 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 65 Issue: 31
  • Publication Date: 2009
  • Doi Number: 10.1016/j.tet.2009.05.090
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.5973-5976


We hereby report the first preparation of the 3,4-dihydrofuro[3,2-d]pyrimidin-2(1H)-one skeleton formed by two controlled Curtius rearrangements of the corresponding acyl azides, prepared from 2-(2-methoxy-2-oxoethyl)furan-3-carboxylate via the hydrazide. Rearrangement of the acyl azides followed by trapping by nucleophiles and intramolecular trapping provided the target compounds. (C) 2009 Elsevier Ltd. All rights reserved.