Application of O-sulfonic acid poly(4-vinylpyrrolidonium) chloride as an efficient polymer-supported catalyst in the rapid synthesis of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products
In this work, a series of 2 H -indazolo[2,1-b]phthalazine-triones and Biginelli-like products were efficiently synthesized for the first time using O-Sulfonic acid poly(4-vinylpyrrolidonium) chloride ([PVP-SO 3 H]Cl) as an eco-friendly polymer-supported catalyst. At first, the catalyst preparation p...
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creator | Dalil Heirati, Seyedeh Zahra Shirini, Farhad Fallah Shojaei, Abdollah |
description | In this work, a series of 2
H
-indazolo[2,1-b]phthalazine-triones and Biginelli-like products were efficiently synthesized for the first time using O-Sulfonic acid poly(4-vinylpyrrolidonium) chloride ([PVP-SO
3
H]Cl) as an eco-friendly polymer-supported catalyst. At first, the catalyst preparation process was optimized based on the chlorosulfonic acid amount and the sulfonation time to obtain a catalyst with the maximum acidity content. The maximum acidity content for [PVP-SO
3
H]Cl was obtained to be 3.31 mmol g
−1
. Then, the optimized [PVP-SO
3
H]Cl was used as a catalyst for the synthesis of a series of 2
H
-indazolo[2,1-b]phthalazine-triones and Biginelli-like products. It was observed that only 10 mg of the catalyst was enough to catalyze these reactions under mild conditions, and the corresponding products were obtained in high to excellent yields. Moreover, the catalyst could be repeatedly used for at least five times without a noticeable decrease in its catalytic activity. |
doi_str_mv | 10.1007/s13738-020-01982-3 |
format | Article |
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H
-indazolo[2,1-b]phthalazine-triones and Biginelli-like products were efficiently synthesized for the first time using O-Sulfonic acid poly(4-vinylpyrrolidonium) chloride ([PVP-SO
3
H]Cl) as an eco-friendly polymer-supported catalyst. At first, the catalyst preparation process was optimized based on the chlorosulfonic acid amount and the sulfonation time to obtain a catalyst with the maximum acidity content. The maximum acidity content for [PVP-SO
3
H]Cl was obtained to be 3.31 mmol g
−1
. Then, the optimized [PVP-SO
3
H]Cl was used as a catalyst for the synthesis of a series of 2
H
-indazolo[2,1-b]phthalazine-triones and Biginelli-like products. It was observed that only 10 mg of the catalyst was enough to catalyze these reactions under mild conditions, and the corresponding products were obtained in high to excellent yields. Moreover, the catalyst could be repeatedly used for at least five times without a noticeable decrease in its catalytic activity.</description><identifier>ISSN: 1735-207X</identifier><identifier>EISSN: 1735-2428</identifier><identifier>DOI: 10.1007/s13738-020-01982-3</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Analytical Chemistry ; Biochemistry ; Catalysts ; Catalytic activity ; Chemical reactions ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chlorides ; Inorganic Chemistry ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Sulfonic acid</subject><ispartof>Journal of the Iranian Chemical Society, 2020-12, Vol.17 (12), p.3217-3225</ispartof><rights>Iranian Chemical Society 2020</rights><rights>Iranian Chemical Society 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-35e8340a0212dd370f2f213966e5da8c0ed6f290ae32d07cd9fa9d870bb6194a3</citedby><cites>FETCH-LOGICAL-c356t-35e8340a0212dd370f2f213966e5da8c0ed6f290ae32d07cd9fa9d870bb6194a3</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/s13738-020-01982-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s13738-020-01982-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,41487,42556,51318</link.rule.ids></links><search><creatorcontrib>Dalil Heirati, Seyedeh Zahra</creatorcontrib><creatorcontrib>Shirini, Farhad</creatorcontrib><creatorcontrib>Fallah Shojaei, Abdollah</creatorcontrib><title>Application of O-sulfonic acid poly(4-vinylpyrrolidonium) chloride as an efficient polymer-supported catalyst in the rapid synthesis of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products</title><title>Journal of the Iranian Chemical Society</title><addtitle>J IRAN CHEM SOC</addtitle><description>In this work, a series of 2
H
-indazolo[2,1-b]phthalazine-triones and Biginelli-like products were efficiently synthesized for the first time using O-Sulfonic acid poly(4-vinylpyrrolidonium) chloride ([PVP-SO
3
H]Cl) as an eco-friendly polymer-supported catalyst. At first, the catalyst preparation process was optimized based on the chlorosulfonic acid amount and the sulfonation time to obtain a catalyst with the maximum acidity content. The maximum acidity content for [PVP-SO
3
H]Cl was obtained to be 3.31 mmol g
−1
. Then, the optimized [PVP-SO
3
H]Cl was used as a catalyst for the synthesis of a series of 2
H
-indazolo[2,1-b]phthalazine-triones and Biginelli-like products. It was observed that only 10 mg of the catalyst was enough to catalyze these reactions under mild conditions, and the corresponding products were obtained in high to excellent yields. Moreover, the catalyst could be repeatedly used for at least five times without a noticeable decrease in its catalytic activity.</description><subject>Analytical Chemistry</subject><subject>Biochemistry</subject><subject>Catalysts</subject><subject>Catalytic activity</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chlorides</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Sulfonic acid</subject><issn>1735-207X</issn><issn>1735-2428</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kc1KXTEUhQ-lQq32BToKdKLQ6E5yfodWbC0ITiwUSgm5-fHG5iZpkiMc37Bv1Vyv4sxRdrLX-lZgNc1HAicEYDjNhA1sxEABA5lGitmbZp8MrMO0pePb5xmGn--a9znfAXQDdO1-8-8sRmelKDZ4FAy6xnl2JngrkZBWoRjcctTie-sXF5eUgrOqbufNMZJrF5JVGomMhEfaGCut9uXRs9GpkmIMqWiFKl-4JRdkPSprjZKIlZ0XXy_Z5m0wvcTWK_EQXPhFPxO8-h3XZS2ceLBe45Lq__Q2R6Ev9rY-OWexs380iimoWZZ82OwZ4bL-8HQeND--XtycX-Kr62_fz8-usGRdXzDr9MhaEEAJVYoNYKihhE19rzslRgla9YZOIDSjCgapJiMmNQ6wWvVkagU7aD7tuDX476xz4XdhTr5GctrWEkjfQ1tVdKeSKeSctOEx2Y1ICyfAt5XxXWW8VsYfK-OsmtjOlKvY3-r0gn7F9R-LJp6T</recordid><startdate>20201201</startdate><enddate>20201201</enddate><creator>Dalil Heirati, Seyedeh Zahra</creator><creator>Shirini, Farhad</creator><creator>Fallah Shojaei, Abdollah</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20201201</creationdate><title>Application of O-sulfonic acid poly(4-vinylpyrrolidonium) chloride as an efficient polymer-supported catalyst in the rapid synthesis of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products</title><author>Dalil Heirati, Seyedeh Zahra ; Shirini, Farhad ; Fallah Shojaei, Abdollah</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-35e8340a0212dd370f2f213966e5da8c0ed6f290ae32d07cd9fa9d870bb6194a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Analytical Chemistry</topic><topic>Biochemistry</topic><topic>Catalysts</topic><topic>Catalytic activity</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chlorides</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Sulfonic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dalil Heirati, Seyedeh Zahra</creatorcontrib><creatorcontrib>Shirini, Farhad</creatorcontrib><creatorcontrib>Fallah Shojaei, Abdollah</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>Dalil Heirati, Seyedeh Zahra</au><au>Shirini, Farhad</au><au>Fallah Shojaei, Abdollah</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Application of O-sulfonic acid poly(4-vinylpyrrolidonium) chloride as an efficient polymer-supported catalyst in the rapid synthesis of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products</atitle><jtitle>Journal of the Iranian Chemical Society</jtitle><stitle>J IRAN CHEM SOC</stitle><date>2020-12-01</date><risdate>2020</risdate><volume>17</volume><issue>12</issue><spage>3217</spage><epage>3225</epage><pages>3217-3225</pages><issn>1735-207X</issn><eissn>1735-2428</eissn><abstract>In this work, a series of 2
H
-indazolo[2,1-b]phthalazine-triones and Biginelli-like products were efficiently synthesized for the first time using O-Sulfonic acid poly(4-vinylpyrrolidonium) chloride ([PVP-SO
3
H]Cl) as an eco-friendly polymer-supported catalyst. At first, the catalyst preparation process was optimized based on the chlorosulfonic acid amount and the sulfonation time to obtain a catalyst with the maximum acidity content. The maximum acidity content for [PVP-SO
3
H]Cl was obtained to be 3.31 mmol g
−1
. Then, the optimized [PVP-SO
3
H]Cl was used as a catalyst for the synthesis of a series of 2
H
-indazolo[2,1-b]phthalazine-triones and Biginelli-like products. It was observed that only 10 mg of the catalyst was enough to catalyze these reactions under mild conditions, and the corresponding products were obtained in high to excellent yields. Moreover, the catalyst could be repeatedly used for at least five times without a noticeable decrease in its catalytic activity.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s13738-020-01982-3</doi><tpages>9</tpages></addata></record> |
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subjects | Analytical Chemistry Biochemistry Catalysts Catalytic activity Chemical reactions Chemical synthesis Chemistry Chemistry and Materials Science Chlorides Inorganic Chemistry Organic Chemistry Original Paper Physical Chemistry Sulfonic acid |
title | Application of O-sulfonic acid poly(4-vinylpyrrolidonium) chloride as an efficient polymer-supported catalyst in the rapid synthesis of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products |
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