A green and efficient synthesis of isoxazol-5(4H)-one derivatives in water and a DFT study
A series of 4-arylmethylene-3-methylisoxazol-5(4 H )-one derivatives are obtained via treating ethyl acetoacetate, hydroxylamine hydrochloride and variety of aromatic aldehyde compounds in the presence of antimony trichloride as an efficient catalyst in aqueous media. Mild conditions, safe, short re...
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| Veröffentlicht in: | Journal of the Iranian Chemical Society 2018-02, Vol.15 (2), p.455-469 |
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| container_title | Journal of the Iranian Chemical Society |
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| creator | Pourmousavi, Seied Ali Fattahi, Hamid Reza Ghorbani, Fatemeh Kanaani, Ayoub Ajloo, Davood |
| description | A series of 4-arylmethylene-3-methylisoxazol-5(4
H
)-one derivatives are obtained via treating ethyl acetoacetate, hydroxylamine hydrochloride and variety of aromatic aldehyde compounds in the presence of antimony trichloride as an efficient catalyst in aqueous media. Mild conditions, safe, short reaction times, commercially available catalyst, environmentally friendly, no uses of organic solvent and high yields are remarkable advantages to this process. (Z)-4-(3-hydroxybenzylidene)-3-methylisoxazol-5(4
H
)-one, (HBIM), is characterized by theoretical (density functional theory) and experimental (IR,
1
H NMR, CV and UV). The structural parameters, vibrational frequencies, molecular electrostatic potential, frontier molecular orbital analysis (HOMO–LUMO), thermodynamic properties and nonlinear optical properties are found and discussed. UV–Vis spectra are recorded in two organic solvents. Thermal stability of HBIM is studied by thermogravimetric analysis. The molecule orbital contributions are studied using the total and partial density of states (TDOS and PDOS). |
| doi_str_mv | 10.1007/s13738-017-1246-2 |
| format | Article |
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H
)-one derivatives are obtained via treating ethyl acetoacetate, hydroxylamine hydrochloride and variety of aromatic aldehyde compounds in the presence of antimony trichloride as an efficient catalyst in aqueous media. Mild conditions, safe, short reaction times, commercially available catalyst, environmentally friendly, no uses of organic solvent and high yields are remarkable advantages to this process. (Z)-4-(3-hydroxybenzylidene)-3-methylisoxazol-5(4
H
)-one, (HBIM), is characterized by theoretical (density functional theory) and experimental (IR,
1
H NMR, CV and UV). The structural parameters, vibrational frequencies, molecular electrostatic potential, frontier molecular orbital analysis (HOMO–LUMO), thermodynamic properties and nonlinear optical properties are found and discussed. UV–Vis spectra are recorded in two organic solvents. Thermal stability of HBIM is studied by thermogravimetric analysis. The molecule orbital contributions are studied using the total and partial density of states (TDOS and PDOS).</description><identifier>ISSN: 1735-207X</identifier><identifier>EISSN: 1735-2428</identifier><identifier>DOI: 10.1007/s13738-017-1246-2</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Analytical Chemistry ; Antimony compounds ; Aromatic compounds ; Biochemistry ; Catalysis ; Catalysts ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Density functional theory ; Derivatives ; Inorganic Chemistry ; Molecular orbitals ; NMR ; Nuclear magnetic resonance ; Optical properties ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Stability analysis ; Thermal stability ; Thermodynamic properties ; Thermogravimetric analysis</subject><ispartof>Journal of the Iranian Chemical Society, 2018-02, Vol.15 (2), p.455-469</ispartof><rights>Iranian Chemical Society 2017</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-a22b2a77a5162e865572b426f499a7e8ac9cf5fc630bf07b81425e48d1481ab13</citedby><cites>FETCH-LOGICAL-c316t-a22b2a77a5162e865572b426f499a7e8ac9cf5fc630bf07b81425e48d1481ab13</cites><orcidid>0000-0003-2217-4346</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s13738-017-1246-2$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s13738-017-1246-2$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,41487,42556,51318</link.rule.ids></links><search><creatorcontrib>Pourmousavi, Seied Ali</creatorcontrib><creatorcontrib>Fattahi, Hamid Reza</creatorcontrib><creatorcontrib>Ghorbani, Fatemeh</creatorcontrib><creatorcontrib>Kanaani, Ayoub</creatorcontrib><creatorcontrib>Ajloo, Davood</creatorcontrib><title>A green and efficient synthesis of isoxazol-5(4H)-one derivatives in water and a DFT study</title><title>Journal of the Iranian Chemical Society</title><addtitle>J IRAN CHEM SOC</addtitle><description>A series of 4-arylmethylene-3-methylisoxazol-5(4
H
)-one derivatives are obtained via treating ethyl acetoacetate, hydroxylamine hydrochloride and variety of aromatic aldehyde compounds in the presence of antimony trichloride as an efficient catalyst in aqueous media. Mild conditions, safe, short reaction times, commercially available catalyst, environmentally friendly, no uses of organic solvent and high yields are remarkable advantages to this process. (Z)-4-(3-hydroxybenzylidene)-3-methylisoxazol-5(4
H
)-one, (HBIM), is characterized by theoretical (density functional theory) and experimental (IR,
1
H NMR, CV and UV). The structural parameters, vibrational frequencies, molecular electrostatic potential, frontier molecular orbital analysis (HOMO–LUMO), thermodynamic properties and nonlinear optical properties are found and discussed. UV–Vis spectra are recorded in two organic solvents. Thermal stability of HBIM is studied by thermogravimetric analysis. The molecule orbital contributions are studied using the total and partial density of states (TDOS and PDOS).</description><subject>Analytical Chemistry</subject><subject>Antimony compounds</subject><subject>Aromatic compounds</subject><subject>Biochemistry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Density functional theory</subject><subject>Derivatives</subject><subject>Inorganic Chemistry</subject><subject>Molecular orbitals</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Optical properties</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Stability analysis</subject><subject>Thermal stability</subject><subject>Thermodynamic properties</subject><subject>Thermogravimetric analysis</subject><issn>1735-207X</issn><issn>1735-2428</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kLFOwzAQhi0EEqXwAGyWWGAw2I4dO2NVKEVCYikSYrGc5FxcFafYaaE8PSkBiYXpbvi__3QfQqeMXjJK1VVimco0oUwRxkVO-B4aMJVJwgXX-787VU-H6CilBaVSUSkG6HmE5xEgYBtqDM75ykNocdqG9gWST7hx2Kfmw342SyLPxfSCNAFwDdFvbOs3kLAP-N22EL8rLL6ezHBq1_X2GB04u0xw8jOH6HFyMxtPyf3D7d14dE-qjOUtsZyX3CplJcs56FxKxUvBcyeKwirQtioqJ12VZ7R0VJWaCS5B6JoJzWzJsiE663tXsXlbQ2rNolnH0J00rNBKKy6674eI9akqNilFcGYV_auNW8Oo2Sk0vULTKTQ7hYZ3DO-Z1GXDHOKf5n-hLz5vciY</recordid><startdate>20180201</startdate><enddate>20180201</enddate><creator>Pourmousavi, Seied Ali</creator><creator>Fattahi, Hamid Reza</creator><creator>Ghorbani, Fatemeh</creator><creator>Kanaani, Ayoub</creator><creator>Ajloo, Davood</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2217-4346</orcidid></search><sort><creationdate>20180201</creationdate><title>A green and efficient synthesis of isoxazol-5(4H)-one derivatives in water and a DFT study</title><author>Pourmousavi, Seied Ali ; Fattahi, Hamid Reza ; Ghorbani, Fatemeh ; Kanaani, Ayoub ; Ajloo, Davood</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-a22b2a77a5162e865572b426f499a7e8ac9cf5fc630bf07b81425e48d1481ab13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Analytical Chemistry</topic><topic>Antimony compounds</topic><topic>Aromatic compounds</topic><topic>Biochemistry</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Density functional theory</topic><topic>Derivatives</topic><topic>Inorganic Chemistry</topic><topic>Molecular orbitals</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Optical properties</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Stability analysis</topic><topic>Thermal stability</topic><topic>Thermodynamic properties</topic><topic>Thermogravimetric analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pourmousavi, Seied Ali</creatorcontrib><creatorcontrib>Fattahi, Hamid Reza</creatorcontrib><creatorcontrib>Ghorbani, Fatemeh</creatorcontrib><creatorcontrib>Kanaani, Ayoub</creatorcontrib><creatorcontrib>Ajloo, Davood</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of the Iranian Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pourmousavi, Seied Ali</au><au>Fattahi, Hamid Reza</au><au>Ghorbani, Fatemeh</au><au>Kanaani, Ayoub</au><au>Ajloo, Davood</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A green and efficient synthesis of isoxazol-5(4H)-one derivatives in water and a DFT study</atitle><jtitle>Journal of the Iranian Chemical Society</jtitle><stitle>J IRAN CHEM SOC</stitle><date>2018-02-01</date><risdate>2018</risdate><volume>15</volume><issue>2</issue><spage>455</spage><epage>469</epage><pages>455-469</pages><issn>1735-207X</issn><eissn>1735-2428</eissn><abstract>A series of 4-arylmethylene-3-methylisoxazol-5(4
H
)-one derivatives are obtained via treating ethyl acetoacetate, hydroxylamine hydrochloride and variety of aromatic aldehyde compounds in the presence of antimony trichloride as an efficient catalyst in aqueous media. Mild conditions, safe, short reaction times, commercially available catalyst, environmentally friendly, no uses of organic solvent and high yields are remarkable advantages to this process. (Z)-4-(3-hydroxybenzylidene)-3-methylisoxazol-5(4
H
)-one, (HBIM), is characterized by theoretical (density functional theory) and experimental (IR,
1
H NMR, CV and UV). The structural parameters, vibrational frequencies, molecular electrostatic potential, frontier molecular orbital analysis (HOMO–LUMO), thermodynamic properties and nonlinear optical properties are found and discussed. UV–Vis spectra are recorded in two organic solvents. Thermal stability of HBIM is studied by thermogravimetric analysis. The molecule orbital contributions are studied using the total and partial density of states (TDOS and PDOS).</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s13738-017-1246-2</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0003-2217-4346</orcidid></addata></record> |
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| subjects | Analytical Chemistry Antimony compounds Aromatic compounds Biochemistry Catalysis Catalysts Chemical synthesis Chemistry Chemistry and Materials Science Density functional theory Derivatives Inorganic Chemistry Molecular orbitals NMR Nuclear magnetic resonance Optical properties Organic Chemistry Original Paper Physical Chemistry Stability analysis Thermal stability Thermodynamic properties Thermogravimetric analysis |
| title | A green and efficient synthesis of isoxazol-5(4H)-one derivatives in water and a DFT study |
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