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

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Koza G., Ozcan S., Şahin E., Balci M.

TETRAHEDRON, vol.65, pp.5973-5976, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 65
  • Publication Date: 2009
  • Doi Number: 10.1016/j.tet.2009.05.090
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5973-5976
  • Keywords: Pyrimidinone, Furopyrimidinone, Acyl azide, Acyl hydrazide, Curtius rearrangement, CALCIUM-CHANNEL BLOCKERS, ACID-ESTERS, DIHYDROPYRIMIDINE, CHEMISTRY, REVISION
  • Bursa Uludag University Affiliated: No

Abstract

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.