SYNTHESIS OF 6-STYRYLDIHYDROPYRIMIDINONES AND 6-STYRYLDIHYDROPYRIDINONES <i>VIA</i> THE RESPECTIVE 6-ALKYLPHOSPHONATES

Authors

  • Rufus Smits Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia; е-mail: rusmits@gmail.com 2 Riga Stradins University,
  • Sergey Belyakov Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia; е-mail: rusmits@gmail.com 2 Riga Stradins University,
  • Marina Petrova Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia; е-mail: rusmits@gmail.com 2 Riga Stradins University,
  • Vladislav Kozhich Riga Stradins University, 16 Dzirciema St., Riga LV-1007, Latvia
  • Ruslan Muhamadejev Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia; е-mail: rusmits@gmail.com 2 Riga Stradins University,

DOI:

https://doi.org/10.1007/6711

Keywords:

alkylphosphonates, dihydropyridinone, dihydropyrimidinone, Arbuzov reaction, bromination, styryl substituent.

Abstract

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.

 

Downloads

Published

2022-12-20

Issue

Vol. 58 No. 12 (2022)

Section

Original Papers