Efficient synthesis of uracil-derived hexa- and tetrahydropyrido[2,3-d] pyrimidines

Nikita Tolstoluzhsky, Pavlo Nikolaienko, Nikolay Gorobets, Erik V. Van Der Eycken, Nadezhda Kolos*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A reaction of 6-amino-1,3-dimethyluracil with 3-(hetero)aroylacrylic acids and their methyl esters leads to hexahydropyrido[2,3-d]pyrimidine-5-carboxylic acids or the corresponding methyl esters in high to excellent yields. One-pot oxidation of the acid derivatives with CAN is accompanied by decarboxylation to give tetrahydropyrido[2,3-d]pyrimidines, while oxidation with bromine resulted in the formation of tetrahydropyrido[2,3-d]pyrimidine-5-carboxylic acids. The aromatization of methyl hexahydropyrido[2,3-d]pyrimidine-5-carboxylates was achieved by K2CO3-mediated air oxidation under ambient conditions. Pyrido[2,3-d]pyrimidines were synthesized in high to excellent yields by condensation of 3-aroylacrylic acids with 6-aminouracil. Further investigation of the reactivity of the products revealed a new application for K2CO3 in the air oxidation of hexahydropyrido[2,3-d] pyrimidines.

Original languageEnglish (US)
Pages (from-to)5364-5369
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number24
DOIs
StatePublished - Aug 1 2013

Keywords

  • 6-Aminouracil
  • Cyclization
  • Michael addition
  • Nitrogen heterocycles
  • Oxidation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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