138278-76-9Relevant academic research and scientific papers
Light-induced one-pot synthesis of pyrimidine derivatives from vinyl azides
Khoroshilova, Olesya V.,Kinzhalov, Mikhail A.,Nguyen, Tuan K.,Rostovskii, Nikolai V.,Titov, Gleb D.
, p. 4971 - 4982 (2020)
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.
