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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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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cited_by cdi_FETCH-LOGICAL-c338t-5cdb1b3aa52d83ba24fdb233cd05c57450b0380120cf05858c05739cbf8328d3
cites cdi_FETCH-LOGICAL-c338t-5cdb1b3aa52d83ba24fdb233cd05c57450b0380120cf05858c05739cbf8328d3
container_end_page 122
container_issue 1
container_start_page 114
container_title Synthetic communications
container_volume 51
creator Shvets, Elena H.
Pidvorotnia, Anastasiia V.
Kulyk, Olesia G.
Mazepa, Alexander V.
Kolosov, Maksim A.
description 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.
doi_str_mv 10.1080/00397911.2020.1821224
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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. 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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. 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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.</abstract><cop>Philadelphia</cop><pub>Taylor &amp; Francis</pub><doi>10.1080/00397911.2020.1821224</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-0303-6941</orcidid><orcidid>https://orcid.org/0000-0002-6714-0513</orcidid><orcidid>https://orcid.org/0000-0003-4791-2114</orcidid></addata></record>
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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
title A straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines
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