Preparation of uracil by cycloreversion. Structure of cycloalkane/ene‐ and norbornane/ene‐fused dihydrouracils

Samuel Frimpong‐Manso, Katalin Nagy, Géza Stájer, Gábor Bernáth, Pál Sohár

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The reactions of the 2‐amino‐1‐cycloalkane‐, cycloalkene‐, norbornane‐ and norbornenecarboxylates 1–9 with potassium cyanate gave urea esters, which were cyclized to cycloalkane‐, cycloalkene‐, norbornane‐ and norbornene‐fused 5,6‐dihydrouracils 10–17. On cyclization, the urea ester formed from trans‐4‐cyclohexene‐1‐carboxylate, furnished the cis‐fused 5,6‐dihydropyrimidine‐2,4(1H,3H)‐dione. On heating, the norbornene‐diexo‐fused dihydrouracil 16 yielded 2,4‐pyrimidinedione through the splitting‐off of cyclopentadiene. The structures of the compounds were proved by 1H and 13C nmr spectroscopy.

Original languageEnglish
Pages (from-to)221-224
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume29
Issue number1
DOIs
Publication statusPublished - Jan 1 1992

ASJC Scopus subject areas

  • Organic Chemistry

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