Synthesis of 2-azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde and its transformations in DMSO

2-Azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde was synthesized by the Vilsmeier–Haack reaction. In DMSO, it transforms into 7-oxo-5-phenyl-4,7-dihydrotetrazolo[1,5- a ]pyrimidine-6-carbaldehyde and then undergoes isomerization recyclization into 6-benzoyltetrazolo[1,5- a ]pyrimidin-7(4 H )-one....

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Bibliographic Details
Published in:Russian chemical bulletin 2024-07, Vol.73 (7), p.2014-2022
Main Authors: Aleksandrova, N. V., Nikolaenkova, E. B., Gatilov, Yu. V., Mamatyuk, V. I., Krivopalov, V. P.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Isomerization
NMR spectroscopy
Organic Chemistry
Vilsmeier-Haack reaction
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Summary:2-Azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde was synthesized by the Vilsmeier–Haack reaction. In DMSO, it transforms into 7-oxo-5-phenyl-4,7-dihydrotetrazolo[1,5- a ]pyrimidine-6-carbaldehyde and then undergoes isomerization recyclization into 6-benzoyltetrazolo[1,5- a ]pyrimidin-7(4 H )-one. The structures of the obtained compounds were determined by NMR spectroscopy and X-ray diffraction.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-024-4321-8