Synthesis of 6-styryldihydropyrimidinones and 6-styryldihydropyridinones via the respective 6-alkylphosphonates

Rufus Smits (Coresponding Author), Sergey Belyakov, Marina Petrova, Vladislav Kozhich, Ruslan Muhamadejev

Research output: Contribution to journalArticlepeer-review


[Figure not available: see fulltext.] Trimethyl or triethyl phosphite in the Arbuzov reaction with 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-one or analogous 6-bromomethyl-3,4-dihydropyridin-2(1H)-one provided the respective 6-alkylphosphonates in excellent yields. The heterocyclic alkylphosphonates are useful synthons in the Horner–Wadsworth–Emmons reaction for introducing a styryl moiety. Bromination of 6-methyl-4-phenyl-3,4-dihydropyridin-2(1H)-one with NBS in methanol resulted in an unexpected compound, while bromination in chloroform with bromine yielded the expected 6-bromomethyl-3,4-dihydropyridin-2(1H)-one, which undergoes facile nucleophilic substitutions. The intermediates and products are validated by single crystal X-ray diffraction.

Original languageEnglish
Pages (from-to)687-694
Number of pages8
JournalChemistry of Heterocyclic Compounds
Issue number12
Publication statusPublished - Dec 2022
Externally publishedYes


  • alkylphosphonates
  • Arbuzov reaction
  • bromination
  • dihydropyridinone
  • dihydropyrimidinone
  • styryl substituent

Field of Science*

  • 1.4 Chemical sciences

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database


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