Pyrimidine-pyridine ring interconversion

H.C. van der Plas

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

This chapter discusses the pyrimidine-to-pyridine ring transformation and pyridine-to-pyrimidine ring transformation. In nucleophile-induced pyrimidine-to-pyridine rearrangements, two types of reactions can be distinguished depending on the structure of the nucleophile: (1) reactions in which the nitrogen in the pyridine ring originates from the nitrogen of the pyrimidine ring or (2) reactions in which the pyridine nitrogen is derived from a nitrogen-containing reagent. In addition to nucleophile-induced transformations, the hetero Diels–Alder (HDA) cycloaddition reactions are also very suitable ways to perform the pyrimidine-to-pyridine ring transformations. To investigate the influence of substituents on the scope of the pyridine-to-pyrimidine ring transformation, a large number of 6-R-2-bromopyridines were investigated in an experiment. It was found that the ring transformation only occurs in quite limited cases. Only the 2-bromo-6-Ph-, 6-OPh- and 6-(substituted-C6H4O)-pyridines could be converted into the corresponding pyrimidine derivatives in reasonable yields (40–50%).
Original languageEnglish
Pages (from-to)31-70
JournalAdvances in Heterocyclic Chemistry
Volume84
Issue numberSuppl.
DOIs
Publication statusPublished - 2003

Keywords

  • diels-alder reactions
  • heterocyclic halogeno compounds
  • nitrogen bridgehead compounds
  • active methylene reagents
  • one-step synthesis
  • potassium-amide
  • liquid-ammonia
  • transformation reactions
  • intramolecular cycloaddition
  • 6-substituted derivatives

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