Green synthesis of novel pyrazolo‐fused benzophenazines using H3PW12O40 as efficient and recyclable catalyst under microwave irradiation
A high‐yield, atom‐efficient, and green protocol for the synthesis of novel pyrazolo‐fused benzophenazines utilizing a multicomponent condensation reaction between 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamine, aromatic aldehydes, and 4‐methylbenzenesulfonohydrazide in the presence of phosphotu...
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| Veröffentlicht in: | Journal of the Chinese Chemical Society (Taipei) 2018-10, Vol.65 (10), p.1259-1265 |
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| creator | Mohebat, Razieh Dehgan, Parisa Yazdani‐Elah‐Abadi, Afshin |
| description | A high‐yield, atom‐efficient, and green protocol for the synthesis of novel pyrazolo‐fused benzophenazines utilizing a multicomponent condensation reaction between 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamine, aromatic aldehydes, and 4‐methylbenzenesulfonohydrazide in the presence of phosphotungstic acid (H3PW12O40) under microwave irradiation (MWI) in EtOH is reported. We provide a novel series of 1H‐benzo[a]pyrazolo[3,4‐c]phenazine derivatives interesting for biological screening tests. This protocol offers several advantages satisfying many principles of green chemistry, including atom economy, energy saving, clean reactions, inexpensive reagents, reusability of H3PW12O40, the absence of any tedious work‐up or purification, and avoidance of hazardous or toxic reagents/catalysts/solvents.
A high‐yielding, atom‐efficient, and green protocol for the synthesis of novel pyrazolo‐fused benzophenazines utilizing a multicomponent condensation reaction between 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamine, aromatic aldehydes, and 4‐methylbenzenesulfonohydrazide in the presence of phosphotungstic acid (H3PW12O40) under microwave irradiation (MWI) in EtOH is reported. The novel series of 1H‐benzo[a]pyrazolo[3,4‐c]phenazine derivatives may be useful for biological screening tests. |
| doi_str_mv | 10.1002/jccs.201800071 |
| format | Article |
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A high‐yielding, atom‐efficient, and green protocol for the synthesis of novel pyrazolo‐fused benzophenazines utilizing a multicomponent condensation reaction between 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamine, aromatic aldehydes, and 4‐methylbenzenesulfonohydrazide in the presence of phosphotungstic acid (H3PW12O40) under microwave irradiation (MWI) in EtOH is reported. The novel series of 1H‐benzo[a]pyrazolo[3,4‐c]phenazine derivatives may be useful for biological screening tests.</description><identifier>ISSN: 0009-4536</identifier><identifier>EISSN: 2192-6549</identifier><identifier>DOI: 10.1002/jccs.201800071</identifier><language>eng</language><publisher>Weinheim: Wiley‐VCH Verlag GmbH & Co. KGaA</publisher><subject>Aldehydes ; benzophenazine ; Catalysis ; Catalysts ; Chemical synthesis ; Clean energy ; Diketones ; Energy conservation ; environmentally friendly ; Irradiation ; microwave irradiation ; multicomponent reaction (MCR) ; Organic chemistry ; Phenylenediamine ; phosphotungstic acid ; pyrazole derivative ; Reagents</subject><ispartof>Journal of the Chinese Chemical Society (Taipei), 2018-10, Vol.65 (10), p.1259-1265</ispartof><rights>2018 The Chemical Society Located in Taipei & Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0001-6732-2408 ; 0000-0002-8162-280X</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%2Fjccs.201800071$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjccs.201800071$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Mohebat, Razieh</creatorcontrib><creatorcontrib>Dehgan, Parisa</creatorcontrib><creatorcontrib>Yazdani‐Elah‐Abadi, Afshin</creatorcontrib><title>Green synthesis of novel pyrazolo‐fused benzophenazines using H3PW12O40 as efficient and recyclable catalyst under microwave irradiation</title><title>Journal of the Chinese Chemical Society (Taipei)</title><description>A high‐yield, atom‐efficient, and green protocol for the synthesis of novel pyrazolo‐fused benzophenazines utilizing a multicomponent condensation reaction between 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamine, aromatic aldehydes, and 4‐methylbenzenesulfonohydrazide in the presence of phosphotungstic acid (H3PW12O40) under microwave irradiation (MWI) in EtOH is reported. We provide a novel series of 1H‐benzo[a]pyrazolo[3,4‐c]phenazine derivatives interesting for biological screening tests. This protocol offers several advantages satisfying many principles of green chemistry, including atom economy, energy saving, clean reactions, inexpensive reagents, reusability of H3PW12O40, the absence of any tedious work‐up or purification, and avoidance of hazardous or toxic reagents/catalysts/solvents.
A high‐yielding, atom‐efficient, and green protocol for the synthesis of novel pyrazolo‐fused benzophenazines utilizing a multicomponent condensation reaction between 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamine, aromatic aldehydes, and 4‐methylbenzenesulfonohydrazide in the presence of phosphotungstic acid (H3PW12O40) under microwave irradiation (MWI) in EtOH is reported. The novel series of 1H‐benzo[a]pyrazolo[3,4‐c]phenazine derivatives may be useful for biological screening tests.</description><subject>Aldehydes</subject><subject>benzophenazine</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Clean energy</subject><subject>Diketones</subject><subject>Energy conservation</subject><subject>environmentally friendly</subject><subject>Irradiation</subject><subject>microwave irradiation</subject><subject>multicomponent reaction (MCR)</subject><subject>Organic chemistry</subject><subject>Phenylenediamine</subject><subject>phosphotungstic acid</subject><subject>pyrazole derivative</subject><subject>Reagents</subject><issn>0009-4536</issn><issn>2192-6549</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNo9kE1LxDAYhIMouH5cPQc8V_PZNkdZ_GRBQcVjeZu-XbPUZE1al-7Jsyd_o7_EFcXTMMMwAw8hR5ydcMbE6cLadCIYLxljBd8iE8GNyHKtzDaZbDKTKS3zXbKX0oIxJYU2E_JxGRE9TaPvnzG5RENLfXjDji7HCOvQha_3z3ZI2NAa_Tosn9HD2nlMdEjOz-mVvHvi4lYxColi2zrr0PcUfEMj2tF2UHdILfTQjamng28w0hdnY1jBG1IXIzQOehf8AdlpoUt4-Kf75PHi_GF6lc1uL6-nZ7NsLgrGM8kN6hzqvJQNgs5tYZnUykJd21bmvG1LrmoUIFEVXDFlAJUsRK1Rl6WRcp8c_-4uY3gdMPXVIgzRby4rwQXTWpaGbVrmt7VyHY7VMroXiGPFWfUDu_qBXf3Drm6m0_t_J78BjHF41w</recordid><startdate>201810</startdate><enddate>201810</enddate><creator>Mohebat, Razieh</creator><creator>Dehgan, Parisa</creator><creator>Yazdani‐Elah‐Abadi, Afshin</creator><general>Wiley‐VCH Verlag GmbH & Co. KGaA</general><general>Wiley Subscription Services, Inc</general><scope/><orcidid>https://orcid.org/0000-0001-6732-2408</orcidid><orcidid>https://orcid.org/0000-0002-8162-280X</orcidid></search><sort><creationdate>201810</creationdate><title>Green synthesis of novel pyrazolo‐fused benzophenazines using H3PW12O40 as efficient and recyclable catalyst under microwave irradiation</title><author>Mohebat, Razieh ; Dehgan, Parisa ; Yazdani‐Elah‐Abadi, Afshin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g2701-319e56ab683dea56c7c0354cabbcf361ff814be2a3e4714049ae4372b5e588933</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aldehydes</topic><topic>benzophenazine</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Clean energy</topic><topic>Diketones</topic><topic>Energy conservation</topic><topic>environmentally friendly</topic><topic>Irradiation</topic><topic>microwave irradiation</topic><topic>multicomponent reaction (MCR)</topic><topic>Organic chemistry</topic><topic>Phenylenediamine</topic><topic>phosphotungstic acid</topic><topic>pyrazole derivative</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mohebat, Razieh</creatorcontrib><creatorcontrib>Dehgan, Parisa</creatorcontrib><creatorcontrib>Yazdani‐Elah‐Abadi, Afshin</creatorcontrib><jtitle>Journal of the Chinese Chemical Society (Taipei)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mohebat, Razieh</au><au>Dehgan, Parisa</au><au>Yazdani‐Elah‐Abadi, Afshin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Green synthesis of novel pyrazolo‐fused benzophenazines using H3PW12O40 as efficient and recyclable catalyst under microwave irradiation</atitle><jtitle>Journal of the Chinese Chemical Society (Taipei)</jtitle><date>2018-10</date><risdate>2018</risdate><volume>65</volume><issue>10</issue><spage>1259</spage><epage>1265</epage><pages>1259-1265</pages><issn>0009-4536</issn><eissn>2192-6549</eissn><abstract>A high‐yield, atom‐efficient, and green protocol for the synthesis of novel pyrazolo‐fused benzophenazines utilizing a multicomponent condensation reaction between 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamine, aromatic aldehydes, and 4‐methylbenzenesulfonohydrazide in the presence of phosphotungstic acid (H3PW12O40) under microwave irradiation (MWI) in EtOH is reported. We provide a novel series of 1H‐benzo[a]pyrazolo[3,4‐c]phenazine derivatives interesting for biological screening tests. This protocol offers several advantages satisfying many principles of green chemistry, including atom economy, energy saving, clean reactions, inexpensive reagents, reusability of H3PW12O40, the absence of any tedious work‐up or purification, and avoidance of hazardous or toxic reagents/catalysts/solvents.
A high‐yielding, atom‐efficient, and green protocol for the synthesis of novel pyrazolo‐fused benzophenazines utilizing a multicomponent condensation reaction between 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamine, aromatic aldehydes, and 4‐methylbenzenesulfonohydrazide in the presence of phosphotungstic acid (H3PW12O40) under microwave irradiation (MWI) in EtOH is reported. The novel series of 1H‐benzo[a]pyrazolo[3,4‐c]phenazine derivatives may be useful for biological screening tests.</abstract><cop>Weinheim</cop><pub>Wiley‐VCH Verlag GmbH & Co. KGaA</pub><doi>10.1002/jccs.201800071</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-6732-2408</orcidid><orcidid>https://orcid.org/0000-0002-8162-280X</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aldehydes benzophenazine Catalysis Catalysts Chemical synthesis Clean energy Diketones Energy conservation environmentally friendly Irradiation microwave irradiation multicomponent reaction (MCR) Organic chemistry Phenylenediamine phosphotungstic acid pyrazole derivative Reagents |
| title | Green synthesis of novel pyrazolo‐fused benzophenazines using H3PW12O40 as efficient and recyclable catalyst under microwave irradiation |
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