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An environmentally benign multi-component reaction: regioselective synthesis of fluorinated 2-aminopyridines using diverse properties of the nitro group
An efficient and concise one-pot procedure was developed for the synthesis of two kinds of fluorinated 2-aminopyridine compounds, 4 and 5 , based on the reactions of different types of 1,1-enediamines (EDAMs), 1 , with a variety of benzaldehyde derivatives, 2 , and 1,3-dicarbonyl compounds, 3 , invo...
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| Published in: | Green chemistry : an international journal and green chemistry resource : GC 2019, Vol.21 (6), p.1505-1516 |
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| Main Authors: | , , , , , |
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| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c325t-f83ba41f110f59b1cd85ff34fdd61b12680e94f7b340ca07f5cf6bdc6c4440b43 |
| container_end_page | 1516 |
| container_issue | 6 |
| container_start_page | 1505 |
| container_title | Green chemistry : an international journal and green chemistry resource : GC |
| container_volume | 21 |
| creator | Du, Xuan-Xuan Zi, Quan-Xing Wu, Yu-Meng Jin, Yi Lin, Jun Yan, Sheng-Jiao |
| description | An efficient and concise one-pot procedure was developed for the synthesis of two kinds of fluorinated 2-aminopyridine compounds,
4
and
5
, based on the reactions of different types of 1,1-enediamines (EDAMs),
1
, with a variety of benzaldehyde derivatives,
2
, and 1,3-dicarbonyl compounds,
3
, involving the Knoevenagel, Michael and cyclization reactions under heating. This protocol is especially suitable for efficient and rapid parallel synthesis of fluorinated 2-aminopyridine compounds with pharmacological activity. The usefulness of this environmentally benign, mild, and multicomponent one-pot reaction procedure was demonstrated by easily synthesizing two kinds of fluorinated 2-aminopyridine libraries. |
| doi_str_mv | 10.1039/C8GC03698E |
| format | article |
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4
and
5
, based on the reactions of different types of 1,1-enediamines (EDAMs),
1
, with a variety of benzaldehyde derivatives,
2
, and 1,3-dicarbonyl compounds,
3
, involving the Knoevenagel, Michael and cyclization reactions under heating. This protocol is especially suitable for efficient and rapid parallel synthesis of fluorinated 2-aminopyridine compounds with pharmacological activity. The usefulness of this environmentally benign, mild, and multicomponent one-pot reaction procedure was demonstrated by easily synthesizing two kinds of fluorinated 2-aminopyridine libraries.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/C8GC03698E</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Benign ; Benzaldehyde ; Carbonyl compounds ; Chemical reactions ; Chemical synthesis ; Crystallography ; Fluorination ; Green chemistry ; Pharmacology</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2019, Vol.21 (6), p.1505-1516</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c325t-f83ba41f110f59b1cd85ff34fdd61b12680e94f7b340ca07f5cf6bdc6c4440b43</citedby><cites>FETCH-LOGICAL-c325t-f83ba41f110f59b1cd85ff34fdd61b12680e94f7b340ca07f5cf6bdc6c4440b43</cites><orcidid>0000-0002-2087-6013 ; 0000-0003-2281-1261 ; 0000-0003-0149-2150</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids></links><search><creatorcontrib>Du, Xuan-Xuan</creatorcontrib><creatorcontrib>Zi, Quan-Xing</creatorcontrib><creatorcontrib>Wu, Yu-Meng</creatorcontrib><creatorcontrib>Jin, Yi</creatorcontrib><creatorcontrib>Lin, Jun</creatorcontrib><creatorcontrib>Yan, Sheng-Jiao</creatorcontrib><title>An environmentally benign multi-component reaction: regioselective synthesis of fluorinated 2-aminopyridines using diverse properties of the nitro group</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>An efficient and concise one-pot procedure was developed for the synthesis of two kinds of fluorinated 2-aminopyridine compounds,
4
and
5
, based on the reactions of different types of 1,1-enediamines (EDAMs),
1
, with a variety of benzaldehyde derivatives,
2
, and 1,3-dicarbonyl compounds,
3
, involving the Knoevenagel, Michael and cyclization reactions under heating. This protocol is especially suitable for efficient and rapid parallel synthesis of fluorinated 2-aminopyridine compounds with pharmacological activity. The usefulness of this environmentally benign, mild, and multicomponent one-pot reaction procedure was demonstrated by easily synthesizing two kinds of fluorinated 2-aminopyridine libraries.</description><subject>Benign</subject><subject>Benzaldehyde</subject><subject>Carbonyl compounds</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Crystallography</subject><subject>Fluorination</subject><subject>Green chemistry</subject><subject>Pharmacology</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpFUMtKxDAUDaLgOLrxCwLuhGrSpC93QxlHYcCNrkua3tQMbVKTdGD-xM81OqKrey73PC4HoWtK7ihh1X1dbmrC8qpcn6AF5TlLqrQgp384T8_Rhfc7Qigtcr5AnyuDwey1s2YEE8QwHHALRvcGj_MQdCLtOFkTT9iBkEFb8xBRr62HAeK-B-wPJryD1x5bhdUwW6eNCNDhNBGjNnY6ON1pAx7PXpsed1HkPODJ2Qlc0PAjjBbY6OAs7p2dp0t0psTg4ep3LtHb4_q1fkq2L5vnerVNJEuzkKiStYJTRSlRWdVS2ZWZUoyrrstpS9O8JFBxVbSMEylIoTKp8raTueSck5azJbo5-sZvPmbwodnZ2ZkY2aS0YmnJSVFE1u2RJZ313oFqJqdH4Q4NJc13881_8-wLOy167Q</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Du, Xuan-Xuan</creator><creator>Zi, Quan-Xing</creator><creator>Wu, Yu-Meng</creator><creator>Jin, Yi</creator><creator>Lin, Jun</creator><creator>Yan, Sheng-Jiao</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-2087-6013</orcidid><orcidid>https://orcid.org/0000-0003-2281-1261</orcidid><orcidid>https://orcid.org/0000-0003-0149-2150</orcidid></search><sort><creationdate>2019</creationdate><title>An environmentally benign multi-component reaction: regioselective synthesis of fluorinated 2-aminopyridines using diverse properties of the nitro group</title><author>Du, Xuan-Xuan ; Zi, Quan-Xing ; Wu, Yu-Meng ; Jin, Yi ; Lin, Jun ; Yan, Sheng-Jiao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-f83ba41f110f59b1cd85ff34fdd61b12680e94f7b340ca07f5cf6bdc6c4440b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Benign</topic><topic>Benzaldehyde</topic><topic>Carbonyl compounds</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Crystallography</topic><topic>Fluorination</topic><topic>Green chemistry</topic><topic>Pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Du, Xuan-Xuan</creatorcontrib><creatorcontrib>Zi, Quan-Xing</creatorcontrib><creatorcontrib>Wu, Yu-Meng</creatorcontrib><creatorcontrib>Jin, Yi</creatorcontrib><creatorcontrib>Lin, Jun</creatorcontrib><creatorcontrib>Yan, Sheng-Jiao</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Du, Xuan-Xuan</au><au>Zi, Quan-Xing</au><au>Wu, Yu-Meng</au><au>Jin, Yi</au><au>Lin, Jun</au><au>Yan, Sheng-Jiao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An environmentally benign multi-component reaction: regioselective synthesis of fluorinated 2-aminopyridines using diverse properties of the nitro group</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2019</date><risdate>2019</risdate><volume>21</volume><issue>6</issue><spage>1505</spage><epage>1516</epage><pages>1505-1516</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>An efficient and concise one-pot procedure was developed for the synthesis of two kinds of fluorinated 2-aminopyridine compounds,
4
and
5
, based on the reactions of different types of 1,1-enediamines (EDAMs),
1
, with a variety of benzaldehyde derivatives,
2
, and 1,3-dicarbonyl compounds,
3
, involving the Knoevenagel, Michael and cyclization reactions under heating. This protocol is especially suitable for efficient and rapid parallel synthesis of fluorinated 2-aminopyridine compounds with pharmacological activity. The usefulness of this environmentally benign, mild, and multicomponent one-pot reaction procedure was demonstrated by easily synthesizing two kinds of fluorinated 2-aminopyridine libraries.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C8GC03698E</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-2087-6013</orcidid><orcidid>https://orcid.org/0000-0003-2281-1261</orcidid><orcidid>https://orcid.org/0000-0003-0149-2150</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2019, Vol.21 (6), p.1505-1516 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_proquest_journals_2193284077 |
| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Benign Benzaldehyde Carbonyl compounds Chemical reactions Chemical synthesis Crystallography Fluorination Green chemistry Pharmacology |
| title | An environmentally benign multi-component reaction: regioselective synthesis of fluorinated 2-aminopyridines using diverse properties of the nitro group |
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