γ‐Fe2O3@Cu3Al‐LDH/HEPES a novel heterogeneous amphoteric catalyst for synthesis of annulated pyrazolo[3,4‐d]pyrimidines
An efficient synthetic method for the heterogenization of bifunctional zwitterionic HEPES catalyst on LDH modified γ‐Fe2O3 magnetic nanoparticles (MNPs) was developed to create a novel polar catalytic environment for tandem catalysis. The efficiency of the resulted acid/base bifunctional catalyst (γ...
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Veröffentlicht in: | Applied organometallic chemistry 2022-10, Vol.36 (10), p.n/a |
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description | An efficient synthetic method for the heterogenization of bifunctional zwitterionic HEPES catalyst on LDH modified γ‐Fe2O3 magnetic nanoparticles (MNPs) was developed to create a novel polar catalytic environment for tandem catalysis. The efficiency of the resulted acid/base bifunctional catalyst (γ‐Fe2O3@Cu3Al‐LDH/HEPES) was investigated in Biginelli‐like synthesis of biologically active pyrazolo[3,4‐d]pyrimidines via the cyclocondensation of 3‐methyl, 1‐phenyl‐H1‐pyrazole‐5‐ol with various aromatic aldehydes and urea derivatives in a mixture of water and ethanol (1:1) under reflux conditions. Besides, the desired products were reached with high conversions and powerful reusability. Utilization of simple and mild reaction conditions, hybrid bifunctional catalytic groups, short reaction time, green and safe solvent, high catalytic performance and good recyclability, easy purification of the products, and simple magnetically work‐up make this methodology an interesting and effective option in the Biginelli reaction.
Magnetic LDH‐coated zwitterionic HEPES catalyst (γ‐Fe2O3@Cu3Al‐LDH/HEPES) is synthesized and characterized as an efficient heterogenized zwitterionic nanocatalyst for the synthesis of some novel biologically active pyrazolo[3,4‐d]pyrimidines by one‐pot direct Biginelli‐like reaction of 3‐methyl, 1‐phenyl‐H1‐pyrazole‐5‐ol with various aromatic aldehydes and urea derivatives in aqueous ethanol under reflux conditions. |
doi_str_mv | 10.1002/aoc.6823 |
format | Article |
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Magnetic LDH‐coated zwitterionic HEPES catalyst (γ‐Fe2O3@Cu3Al‐LDH/HEPES) is synthesized and characterized as an efficient heterogenized zwitterionic nanocatalyst for the synthesis of some novel biologically active pyrazolo[3,4‐d]pyrimidines by one‐pot direct Biginelli‐like reaction of 3‐methyl, 1‐phenyl‐H1‐pyrazole‐5‐ol with various aromatic aldehydes and urea derivatives in aqueous ethanol under reflux conditions.</description><identifier>ISSN: 0268-2605</identifier><identifier>EISSN: 1099-0739</identifier><identifier>DOI: 10.1002/aoc.6823</identifier><language>eng</language><subject>aqueous synthesis ; Biginelli reaction ; pyrazolo[3,4‐d]pyrimidines ; zwitterionic catalyst ; γ‐Fe2O3@Cu3Al‐LDH/HEPES</subject><ispartof>Applied organometallic chemistry, 2022-10, Vol.36 (10), p.n/a</ispartof><rights>2022 John Wiley & Sons Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-7740-7234 ; 0000-0002-1043-3470 ; 0000-0002-5724-3199 ; 0000-0002-7331-2748</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Faoc.6823$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Faoc.6823$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Ghobakhloo, Farzaneh</creatorcontrib><creatorcontrib>Azarifar, Davood</creatorcontrib><creatorcontrib>Mohammadi, Masoud</creatorcontrib><creatorcontrib>Ghaemi, Masoumeh</creatorcontrib><title>γ‐Fe2O3@Cu3Al‐LDH/HEPES a novel heterogeneous amphoteric catalyst for synthesis of annulated pyrazolo[3,4‐d]pyrimidines</title><title>Applied organometallic chemistry</title><description>An efficient synthetic method for the heterogenization of bifunctional zwitterionic HEPES catalyst on LDH modified γ‐Fe2O3 magnetic nanoparticles (MNPs) was developed to create a novel polar catalytic environment for tandem catalysis. The efficiency of the resulted acid/base bifunctional catalyst (γ‐Fe2O3@Cu3Al‐LDH/HEPES) was investigated in Biginelli‐like synthesis of biologically active pyrazolo[3,4‐d]pyrimidines via the cyclocondensation of 3‐methyl, 1‐phenyl‐H1‐pyrazole‐5‐ol with various aromatic aldehydes and urea derivatives in a mixture of water and ethanol (1:1) under reflux conditions. Besides, the desired products were reached with high conversions and powerful reusability. Utilization of simple and mild reaction conditions, hybrid bifunctional catalytic groups, short reaction time, green and safe solvent, high catalytic performance and good recyclability, easy purification of the products, and simple magnetically work‐up make this methodology an interesting and effective option in the Biginelli reaction.
Magnetic LDH‐coated zwitterionic HEPES catalyst (γ‐Fe2O3@Cu3Al‐LDH/HEPES) is synthesized and characterized as an efficient heterogenized zwitterionic nanocatalyst for the synthesis of some novel biologically active pyrazolo[3,4‐d]pyrimidines by one‐pot direct Biginelli‐like reaction of 3‐methyl, 1‐phenyl‐H1‐pyrazole‐5‐ol with various aromatic aldehydes and urea derivatives in aqueous ethanol under reflux conditions.</description><subject>aqueous synthesis</subject><subject>Biginelli reaction</subject><subject>pyrazolo[3,4‐d]pyrimidines</subject><subject>zwitterionic catalyst</subject><subject>γ‐Fe2O3@Cu3Al‐LDH/HEPES</subject><issn>0268-2605</issn><issn>1099-0739</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNotkF1KAzEUhYMoWKvgErIAp71J5i9vlrG1QqGC-iQy3EkydiSdlMm0Mj6IS3Av7sNFuBKn6NPhnIePw0fIOYMRA-BjdGoUp1wckAEDKQNIhDwkA-BxGvAYomNy4v0LAMiYhQPy_v318_E5M3wpLrOtmNi-La7m4_n0dnpHkdZuZyxdmdY07tnUxm09xfVm5fqhUlRhi7bzLS1dQ31XtyvjK09dSbGutxZbo-mma_DNWfcoLsKerp_6oVpXuqqNPyVHJVpvzv5zSB5m0_tsHiyW1zfZZBF4JoUIOKpQRNKEhdGguChQp0nBAZDxVCrBTCHLWOpSJ6oQGGkM4yKEJOUq5pGUYkiCP-5rZU2Xb_oD2HQ5g3wvLe-l5Xtp-WSZ7VP8Ar9NZlU</recordid><startdate>202210</startdate><enddate>202210</enddate><creator>Ghobakhloo, Farzaneh</creator><creator>Azarifar, Davood</creator><creator>Mohammadi, Masoud</creator><creator>Ghaemi, Masoumeh</creator><scope/><orcidid>https://orcid.org/0000-0002-7740-7234</orcidid><orcidid>https://orcid.org/0000-0002-1043-3470</orcidid><orcidid>https://orcid.org/0000-0002-5724-3199</orcidid><orcidid>https://orcid.org/0000-0002-7331-2748</orcidid></search><sort><creationdate>202210</creationdate><title>γ‐Fe2O3@Cu3Al‐LDH/HEPES a novel heterogeneous amphoteric catalyst for synthesis of annulated pyrazolo[3,4‐d]pyrimidines</title><author>Ghobakhloo, Farzaneh ; Azarifar, Davood ; Mohammadi, Masoud ; Ghaemi, Masoumeh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-s1933-2ac4359e4bed0c23bad87b200a1289c31eb9f69dfd7cb3a5da46b40782c625993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>aqueous synthesis</topic><topic>Biginelli reaction</topic><topic>pyrazolo[3,4‐d]pyrimidines</topic><topic>zwitterionic catalyst</topic><topic>γ‐Fe2O3@Cu3Al‐LDH/HEPES</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ghobakhloo, Farzaneh</creatorcontrib><creatorcontrib>Azarifar, Davood</creatorcontrib><creatorcontrib>Mohammadi, Masoud</creatorcontrib><creatorcontrib>Ghaemi, Masoumeh</creatorcontrib><jtitle>Applied organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ghobakhloo, Farzaneh</au><au>Azarifar, Davood</au><au>Mohammadi, Masoud</au><au>Ghaemi, Masoumeh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>γ‐Fe2O3@Cu3Al‐LDH/HEPES a novel heterogeneous amphoteric catalyst for synthesis of annulated pyrazolo[3,4‐d]pyrimidines</atitle><jtitle>Applied organometallic chemistry</jtitle><date>2022-10</date><risdate>2022</risdate><volume>36</volume><issue>10</issue><epage>n/a</epage><issn>0268-2605</issn><eissn>1099-0739</eissn><abstract>An efficient synthetic method for the heterogenization of bifunctional zwitterionic HEPES catalyst on LDH modified γ‐Fe2O3 magnetic nanoparticles (MNPs) was developed to create a novel polar catalytic environment for tandem catalysis. The efficiency of the resulted acid/base bifunctional catalyst (γ‐Fe2O3@Cu3Al‐LDH/HEPES) was investigated in Biginelli‐like synthesis of biologically active pyrazolo[3,4‐d]pyrimidines via the cyclocondensation of 3‐methyl, 1‐phenyl‐H1‐pyrazole‐5‐ol with various aromatic aldehydes and urea derivatives in a mixture of water and ethanol (1:1) under reflux conditions. Besides, the desired products were reached with high conversions and powerful reusability. Utilization of simple and mild reaction conditions, hybrid bifunctional catalytic groups, short reaction time, green and safe solvent, high catalytic performance and good recyclability, easy purification of the products, and simple magnetically work‐up make this methodology an interesting and effective option in the Biginelli reaction.
Magnetic LDH‐coated zwitterionic HEPES catalyst (γ‐Fe2O3@Cu3Al‐LDH/HEPES) is synthesized and characterized as an efficient heterogenized zwitterionic nanocatalyst for the synthesis of some novel biologically active pyrazolo[3,4‐d]pyrimidines by one‐pot direct Biginelli‐like reaction of 3‐methyl, 1‐phenyl‐H1‐pyrazole‐5‐ol with various aromatic aldehydes and urea derivatives in aqueous ethanol under reflux conditions.</abstract><doi>10.1002/aoc.6823</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0002-7740-7234</orcidid><orcidid>https://orcid.org/0000-0002-1043-3470</orcidid><orcidid>https://orcid.org/0000-0002-5724-3199</orcidid><orcidid>https://orcid.org/0000-0002-7331-2748</orcidid></addata></record> |
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subjects | aqueous synthesis Biginelli reaction pyrazolo[3,4‐d]pyrimidines zwitterionic catalyst γ‐Fe2O3@Cu3Al‐LDH/HEPES |
title | γ‐Fe2O3@Cu3Al‐LDH/HEPES a novel heterogeneous amphoteric catalyst for synthesis of annulated pyrazolo[3,4‐d]pyrimidines |
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