A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones
A novel dicationic ionic liquid, N , N , N ′, N ′-tetramethyl- N , N ′-bis(sulfo)ethane-1,2-diaminium mesylate [TMBSED][OMs] 2 ), has been produced, and identified by analysis of its 1 H NMR, 13 C NMR, FT-IR, mass and thermal gravimetric data. Thereafter, it has been utilized as a highly effectual,...
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| Veröffentlicht in: | Research on chemical intermediates 2018-10, Vol.44 (10), p.6253-6266 |
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| creator | Irannejad-Gheshlaghchaei, Navid Zare, Abdolkarim Sajadikhah, Seyed Sajad Banaei, Alireza |
| description | A novel dicationic ionic liquid,
N
,
N
,
N
′,
N
′-tetramethyl-
N
,
N
′-bis(sulfo)ethane-1,2-diaminium mesylate [TMBSED][OMs]
2
), has been produced, and identified by analysis of its
1
H NMR,
13
C NMR, FT-IR, mass and thermal gravimetric data. Thereafter, it has been utilized as a highly effectual, homogeneous and dual-functional catalyst to promote the multi-component reaction of ethyl acetoacetate, hydroxylamine hydrochloride and arylaldehydes under solvent-free conditions for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4
H
)-ones. Due to the dual-functionality of [TMBSED][OMs]
2
(possessing acidic and basic sites), and also having two sites of each, it was a highly effective and general catalyst for the synthesis. Moreover, a plausible and attractive mechanism based on the dual-functionality of the catalyst has been proposed.
Graphical Abstract |
| doi_str_mv | 10.1007/s11164-018-3488-8 |
| format | Article |
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N
,
N
,
N
′,
N
′-tetramethyl-
N
,
N
′-bis(sulfo)ethane-1,2-diaminium mesylate [TMBSED][OMs]
2
), has been produced, and identified by analysis of its
1
H NMR,
13
C NMR, FT-IR, mass and thermal gravimetric data. Thereafter, it has been utilized as a highly effectual, homogeneous and dual-functional catalyst to promote the multi-component reaction of ethyl acetoacetate, hydroxylamine hydrochloride and arylaldehydes under solvent-free conditions for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4
H
)-ones. Due to the dual-functionality of [TMBSED][OMs]
2
(possessing acidic and basic sites), and also having two sites of each, it was a highly effective and general catalyst for the synthesis. Moreover, a plausible and attractive mechanism based on the dual-functionality of the catalyst has been proposed.
Graphical Abstract</description><identifier>ISSN: 0922-6168</identifier><identifier>EISSN: 1568-5675</identifier><identifier>DOI: 10.1007/s11164-018-3488-8</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Catalysis ; Catalysts ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Ethane ; Gravimetry ; Inorganic Chemistry ; Ionic liquids ; NMR ; Nuclear magnetic resonance ; Physical Chemistry</subject><ispartof>Research on chemical intermediates, 2018-10, Vol.44 (10), p.6253-6266</ispartof><rights>Springer Science+Business Media B.V., part of Springer Nature 2018</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-a025cb8532455799c3179f2db616301a5c4095ad72083e07d1752d722f78c07a3</citedby><cites>FETCH-LOGICAL-c353t-a025cb8532455799c3179f2db616301a5c4095ad72083e07d1752d722f78c07a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11164-018-3488-8$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11164-018-3488-8$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Irannejad-Gheshlaghchaei, Navid</creatorcontrib><creatorcontrib>Zare, Abdolkarim</creatorcontrib><creatorcontrib>Sajadikhah, Seyed Sajad</creatorcontrib><creatorcontrib>Banaei, Alireza</creatorcontrib><title>A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones</title><title>Research on chemical intermediates</title><addtitle>Res Chem Intermed</addtitle><description>A novel dicationic ionic liquid,
N
,
N
,
N
′,
N
′-tetramethyl-
N
,
N
′-bis(sulfo)ethane-1,2-diaminium mesylate [TMBSED][OMs]
2
), has been produced, and identified by analysis of its
1
H NMR,
13
C NMR, FT-IR, mass and thermal gravimetric data. Thereafter, it has been utilized as a highly effectual, homogeneous and dual-functional catalyst to promote the multi-component reaction of ethyl acetoacetate, hydroxylamine hydrochloride and arylaldehydes under solvent-free conditions for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4
H
)-ones. Due to the dual-functionality of [TMBSED][OMs]
2
(possessing acidic and basic sites), and also having two sites of each, it was a highly effective and general catalyst for the synthesis. Moreover, a plausible and attractive mechanism based on the dual-functionality of the catalyst has been proposed.
Graphical Abstract</description><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Ethane</subject><subject>Gravimetry</subject><subject>Inorganic Chemistry</subject><subject>Ionic liquids</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Physical Chemistry</subject><issn>0922-6168</issn><issn>1568-5675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kM1KxDAUhYMoOP48gLuAG11Eb5KmSZci6giCG12HmCZOhkyjTSvW9_B9zVDBlZv7x_kunIPQCYULCiAvM6W0rghQRXilFFE7aEFFrYiopdhFC2gYIzWt1T46yHkNQIVSsEDfV7hLHy7iNlgzhNQFi-caw_sYWmwyNngVXldxws57Z4fRRGy6FrdlIH7s7BYrt8KbOOUB-9TjYeVwnrrScsg4eczJxg2rKZKKmH6K8-I6R0JOn-YrRUfEWbU8J6lz-QjteROzO_7th-j59ubpekkeHu_ur68eiOWCD8QAE_ZFCc4qIWTTWE5l41n7UoxyoEbYChphWslAcQeypVKwsjEvlQVp-CE6nf--9el9dHnQ6zT2xUzWjELFgPNGFRWdVbZPOffO67c-bIoLTUFv09dz-rqkr7fp6y3DZiYXbffq-r_P_0M_vumH6w</recordid><startdate>20181001</startdate><enddate>20181001</enddate><creator>Irannejad-Gheshlaghchaei, Navid</creator><creator>Zare, Abdolkarim</creator><creator>Sajadikhah, Seyed Sajad</creator><creator>Banaei, Alireza</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20181001</creationdate><title>A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones</title><author>Irannejad-Gheshlaghchaei, Navid ; Zare, Abdolkarim ; Sajadikhah, Seyed Sajad ; Banaei, Alireza</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-a025cb8532455799c3179f2db616301a5c4095ad72083e07d1752d722f78c07a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Ethane</topic><topic>Gravimetry</topic><topic>Inorganic Chemistry</topic><topic>Ionic liquids</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Physical Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Irannejad-Gheshlaghchaei, Navid</creatorcontrib><creatorcontrib>Zare, Abdolkarim</creatorcontrib><creatorcontrib>Sajadikhah, Seyed Sajad</creatorcontrib><creatorcontrib>Banaei, Alireza</creatorcontrib><collection>CrossRef</collection><jtitle>Research on chemical intermediates</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Irannejad-Gheshlaghchaei, Navid</au><au>Zare, Abdolkarim</au><au>Sajadikhah, Seyed Sajad</au><au>Banaei, Alireza</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones</atitle><jtitle>Research on chemical intermediates</jtitle><stitle>Res Chem Intermed</stitle><date>2018-10-01</date><risdate>2018</risdate><volume>44</volume><issue>10</issue><spage>6253</spage><epage>6266</epage><pages>6253-6266</pages><issn>0922-6168</issn><eissn>1568-5675</eissn><abstract>A novel dicationic ionic liquid,
N
,
N
,
N
′,
N
′-tetramethyl-
N
,
N
′-bis(sulfo)ethane-1,2-diaminium mesylate [TMBSED][OMs]
2
), has been produced, and identified by analysis of its
1
H NMR,
13
C NMR, FT-IR, mass and thermal gravimetric data. Thereafter, it has been utilized as a highly effectual, homogeneous and dual-functional catalyst to promote the multi-component reaction of ethyl acetoacetate, hydroxylamine hydrochloride and arylaldehydes under solvent-free conditions for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4
H
)-ones. Due to the dual-functionality of [TMBSED][OMs]
2
(possessing acidic and basic sites), and also having two sites of each, it was a highly effective and general catalyst for the synthesis. Moreover, a plausible and attractive mechanism based on the dual-functionality of the catalyst has been proposed.
Graphical Abstract</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s11164-018-3488-8</doi><tpages>14</tpages></addata></record> |
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| subjects | Catalysis Catalysts Chemical synthesis Chemistry Chemistry and Materials Science Ethane Gravimetry Inorganic Chemistry Ionic liquids NMR Nuclear magnetic resonance Physical Chemistry |
| title | A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones |
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