Abstract

A one-pot procedure for the synthesis of tetrasubstituted dihydropyrimidine and pyrimidine derivatives from α-azidocinnamates was developed. The synthesis is based on the finding that the outcome of LED photolysis of α-azidocinnamates depends on the light wavelength employed. Blue light (455 nm) leads to the formation of 2H-azirines only, but violet light (395 nm), UV-A light (365 nm), or sunlight result in the transformation of the in situ formed 2H-azirines to 1,3-diazabicyclo[3.1.0]hex-3-enes. Under basic catalysis (DBU), the latter were isomerized to 1,6-dihydropyrimidines which were oxidized to pyrimidines using DDQ. A successful use of Cs2CO3 as a base and air as an oxidant was also demonstrated.

Original languageEnglish
Pages (from-to)4971-4982
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number26
DOIs
Publication statusPublished - 14 Jul 2020

Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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