A straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines

4,7-Dihydroazolo[1,5-a]pyrimidin-5-ylmethanesulfonamides are side-products of the three-component Biginelli-like reaction of aminoazoles, aldehydes and N,N-dialkyl-2-ketomethanesulfonamides. Herein, we report a straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrim...

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Bibliographic Details
Published in:Synthetic communications 2021-01, Vol.51 (1), p.114-122
Main Authors: Shvets, Elena H., Pidvorotnia, Anastasiia V., Kulyk, Olesia G., Mazepa, Alexander V., Kolosov, Maksim A.
Format: Article
Language:English
Subjects:
2-ketosulfonamides
4,7-dihydroazolo[1,5-a]pyrimidines
Alcohols
Aldehydes
Biginelli-like reaction
Chemical synthesis
Claisen condensation
Condensates
Esters
Mass spectrometry
N,N-dialkylmethanesulfonamides
NMR
Nuclear magnetic resonance
Oxidation
Pyrimidines
Substitutes
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Summary:4,7-Dihydroazolo[1,5-a]pyrimidin-5-ylmethanesulfonamides are side-products of the three-component Biginelli-like reaction of aminoazoles, aldehydes and N,N-dialkyl-2-ketomethanesulfonamides. Herein, we report a straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines by a two-component condensation of aminoazoles and N,N-dialkyl(cinnamoyl)methanesulfonamides in DMF at reflux. The starting N,N-dialkyl-2-ketomethanesulfonamides can be obtained by either lithiation of N,N-dialkylmethanesulfonamides and reaction with aldehydes followed by oxidation of the resulting alcohols or by Claisen condensation of N,N-dialkylmethanesulfonamides with the corresponding esters. The chemical structures of all synthesized compounds are supported by 1 H and 13 C NMR-spectroscopy, mass spectrometry and elemental analysis.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2020.1821224