An efficient and green synthesis of novel highly functionalized nitrogen-fused pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine derivatives using recyclable choline hydroxide
Choline hydroxide (ChOH) has been found to be a green and efficient basic ionic liquid catalyst for the synthesis of highly functionalized pyrido[2′,3′:3,4]pyrazolo[1,5- a ]pyrimidine derivatives through the reaction of a series of α,β -unsaturated ketones with 1 H -pyrazolo[3,4- b ]pyridin-3-amine...
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Veröffentlicht in: | Research on chemical intermediates 2018-12, Vol.44 (12), p.7311-7329 |
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creator | Krishnammagari, Suresh Kumar Jeong, Yeon Tae |
description | Choline hydroxide (ChOH) has been found to be a green and efficient basic ionic liquid catalyst for the synthesis of highly functionalized pyrido[2′,3′:3,4]pyrazolo[1,5-
a
]pyrimidine derivatives through the reaction of a series of
α,β
-unsaturated ketones with 1
H
-pyrazolo[3,4-
b
]pyridin-3-amine under neat conditions. A series of
α,β
-unsaturated ketones with different substituted functional groups efficiently were converted to their corresponding products in good to excellent isolated yields, and the reactions can be easily scaled up to multigrams. The present environmentally benign and reusable ChOH catalyst offers several advantages such as shorter reaction times, a wide range of functional group tolerance and high yield of products via a simple experimental and work-up procedure.
Graphical abstract
The imparted features of this methodology are the green reaction, simple procedure, reusability, easy workability and high efficiency of ChOH. |
doi_str_mv | 10.1007/s11164-018-3558-y |
format | Article |
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a
]pyrimidine derivatives through the reaction of a series of
α,β
-unsaturated ketones with 1
H
-pyrazolo[3,4-
b
]pyridin-3-amine under neat conditions. A series of
α,β
-unsaturated ketones with different substituted functional groups efficiently were converted to their corresponding products in good to excellent isolated yields, and the reactions can be easily scaled up to multigrams. The present environmentally benign and reusable ChOH catalyst offers several advantages such as shorter reaction times, a wide range of functional group tolerance and high yield of products via a simple experimental and work-up procedure.
Graphical abstract
The imparted features of this methodology are the green reaction, simple procedure, reusability, easy workability and high efficiency of ChOH.</description><identifier>ISSN: 0922-6168</identifier><identifier>EISSN: 1568-5675</identifier><identifier>DOI: 10.1007/s11164-018-3558-y</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Catalysis ; Catalysts ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Choline ; Derivatives ; Functional groups ; Inorganic Chemistry ; Ionic liquids ; Ions ; Ketones ; Physical Chemistry ; Workability</subject><ispartof>Research on chemical intermediates, 2018-12, Vol.44 (12), p.7311-7329</ispartof><rights>Springer Nature B.V. 2018</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-b236c65f4cbc572cd6aa183a25c1263b3af9c10b16347c12d7b6ed4fd2b509263</citedby><cites>FETCH-LOGICAL-c353t-b236c65f4cbc572cd6aa183a25c1263b3af9c10b16347c12d7b6ed4fd2b509263</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/s11164-018-3558-y$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11164-018-3558-y$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Krishnammagari, Suresh Kumar</creatorcontrib><creatorcontrib>Jeong, Yeon Tae</creatorcontrib><title>An efficient and green synthesis of novel highly functionalized nitrogen-fused pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine derivatives using recyclable choline hydroxide</title><title>Research on chemical intermediates</title><addtitle>Res Chem Intermed</addtitle><description>Choline hydroxide (ChOH) has been found to be a green and efficient basic ionic liquid catalyst for the synthesis of highly functionalized pyrido[2′,3′:3,4]pyrazolo[1,5-
a
]pyrimidine derivatives through the reaction of a series of
α,β
-unsaturated ketones with 1
H
-pyrazolo[3,4-
b
]pyridin-3-amine under neat conditions. A series of
α,β
-unsaturated ketones with different substituted functional groups efficiently were converted to their corresponding products in good to excellent isolated yields, and the reactions can be easily scaled up to multigrams. The present environmentally benign and reusable ChOH catalyst offers several advantages such as shorter reaction times, a wide range of functional group tolerance and high yield of products via a simple experimental and work-up procedure.
Graphical abstract
The imparted features of this methodology are the green reaction, simple procedure, reusability, easy workability and high efficiency of ChOH.</description><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Choline</subject><subject>Derivatives</subject><subject>Functional groups</subject><subject>Inorganic Chemistry</subject><subject>Ionic liquids</subject><subject>Ions</subject><subject>Ketones</subject><subject>Physical Chemistry</subject><subject>Workability</subject><issn>0922-6168</issn><issn>1568-5675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1UcuKFTEUDKLgdfQD3AXc3jh5dNJ93Q2Dj4EBN7oaJKSTk-4MbXJNui_2rPwgV36SX2KaK7hycw6nqCqoUwi9ZPQ1o7S9LIwx1RDKOiKk7Mj6CO2YVB2RqpWP0Y4eOCeKqe4pelbKPaVMdh3doZ9XEYP3wQaIMzbR4SEDRFzWOI9QQsHJ45hOMOExDOO0Yr9EO4cUzRQewOEY5pwGiMQvpZ7HNQeX7vjvH7_2oo43Yt98qaB5SFO6Y3tJzHaGr8GFCNhBDiczhxMUvJQQB5zBrnYy_QTYjmnaSOPqcvoeHDxHT7yZCrz4uy_Q53dvP11_ILcf399cX90SK6SYSc-Fskr6xvZWttw6ZQzrhOHSMq5EL4w_WEZ7pkTTVsi1vQLXeMd7Wf-kxAV6dfY95vRtgTLr-7TkmrhozoQ4CKrExmJnls2plAxeH2suk1fNqN5K0edSdC1Fb6XotWr4WVMqNw6Q_zn_X_QHO0qWFA</recordid><startdate>20181201</startdate><enddate>20181201</enddate><creator>Krishnammagari, Suresh Kumar</creator><creator>Jeong, Yeon Tae</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20181201</creationdate><title>An efficient and green synthesis of novel highly functionalized nitrogen-fused pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine derivatives using recyclable choline hydroxide</title><author>Krishnammagari, Suresh Kumar ; Jeong, Yeon Tae</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-b236c65f4cbc572cd6aa183a25c1263b3af9c10b16347c12d7b6ed4fd2b509263</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>Choline</topic><topic>Derivatives</topic><topic>Functional groups</topic><topic>Inorganic Chemistry</topic><topic>Ionic liquids</topic><topic>Ions</topic><topic>Ketones</topic><topic>Physical Chemistry</topic><topic>Workability</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krishnammagari, Suresh Kumar</creatorcontrib><creatorcontrib>Jeong, Yeon Tae</creatorcontrib><collection>CrossRef</collection><jtitle>Research on chemical intermediates</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krishnammagari, Suresh Kumar</au><au>Jeong, Yeon Tae</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An efficient and green synthesis of novel highly functionalized nitrogen-fused pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine derivatives using recyclable choline hydroxide</atitle><jtitle>Research on chemical intermediates</jtitle><stitle>Res Chem Intermed</stitle><date>2018-12-01</date><risdate>2018</risdate><volume>44</volume><issue>12</issue><spage>7311</spage><epage>7329</epage><pages>7311-7329</pages><issn>0922-6168</issn><eissn>1568-5675</eissn><abstract>Choline hydroxide (ChOH) has been found to be a green and efficient basic ionic liquid catalyst for the synthesis of highly functionalized pyrido[2′,3′:3,4]pyrazolo[1,5-
a
]pyrimidine derivatives through the reaction of a series of
α,β
-unsaturated ketones with 1
H
-pyrazolo[3,4-
b
]pyridin-3-amine under neat conditions. A series of
α,β
-unsaturated ketones with different substituted functional groups efficiently were converted to their corresponding products in good to excellent isolated yields, and the reactions can be easily scaled up to multigrams. The present environmentally benign and reusable ChOH catalyst offers several advantages such as shorter reaction times, a wide range of functional group tolerance and high yield of products via a simple experimental and work-up procedure.
Graphical abstract
The imparted features of this methodology are the green reaction, simple procedure, reusability, easy workability and high efficiency of ChOH.</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s11164-018-3558-y</doi><tpages>19</tpages></addata></record> |
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issn | 0922-6168 1568-5675 |
language | eng |
recordid | cdi_proquest_journals_2133930636 |
source | SpringerNature Journals |
subjects | Catalysis Catalysts Chemical synthesis Chemistry Chemistry and Materials Science Choline Derivatives Functional groups Inorganic Chemistry Ionic liquids Ions Ketones Physical Chemistry Workability |
title | An efficient and green synthesis of novel highly functionalized nitrogen-fused pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine derivatives using recyclable choline hydroxide |
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