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Issue 26, 2020
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Light-induced one-pot synthesis of pyrimidine derivatives from vinyl azides

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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.

Graphical abstract: Light-induced one-pot synthesis of pyrimidine derivatives from vinyl azides

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Supplementary files

Article information


Submitted
02 Apr 2020
Accepted
13 Jun 2020
First published
15 Jun 2020

Org. Biomol. Chem., 2020,18, 4971-4982
Article type
Paper

Light-induced one-pot synthesis of pyrimidine derivatives from vinyl azides

T. K. Nguyen, G. D. Titov, O. V. Khoroshilova, M. A. Kinzhalov and N. V. Rostovskii, Org. Biomol. Chem., 2020, 18, 4971
DOI: 10.1039/D0OB00693A

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