An environmentally benign cascade reaction of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives for highly site-selective synthesis of quinolizines and quinolizinium salts in water
A novel protocol for the synthesis of quinolizines ( 3 ) and quinolizinium salts ( 4 ) from chromone-3-carboxaldehydes 1 with ethyl 2-(pyridine-2-yl)acetate derivatives 2 via an unprecedented cascade reaction in water was constructed. As a result, functionalized quinolizines ( 3 ) bearing a chromone...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2020-10, Vol.22 (2), p.6943-6953 |
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| creator | Chen, Li Huang, Rong Li, Kun Yun, Xing-Han Yang, Chang-Long Yan, Sheng-Jiao |
| description | A novel protocol for the synthesis of quinolizines (
3
) and quinolizinium salts (
4
) from chromone-3-carboxaldehydes
1
with ethyl 2-(pyridine-2-yl)acetate derivatives
2
via
an unprecedented cascade reaction in water was constructed. As a result, functionalized quinolizines (
3
) bearing a chromone skeleton were prepared by simple reflux of the mixture of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives in water. Quinolizinium salts (
4
) were also prepared in water under acidic conditions. The formation of quinolizinium salts was accompanied by the formation of two bonds and the cleavage of one bond in a single step. This protocol can be used in the synthesis of a wide variety of quinolizines and quinolizinium salts, and is suitable for combinatorial and parallel syntheses of quinolizine derivatives natural-like products. This approach has several advantages such as the use of an environmentally friendly solvent, simple and practical operation (with filtration and washing without column chromatography separation), excellent yields (83-96%), and formation of a product with potential biological activity.
A protocol for the synthesis of quinolizines from ethyl 2-(pyridine-2-yl)acetates
via
an unprecedented cascade reaction in water was constructed. |
| doi_str_mv | 10.1039/d0gc02460k |
| format | Article |
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3
) and quinolizinium salts (
4
) from chromone-3-carboxaldehydes
1
with ethyl 2-(pyridine-2-yl)acetate derivatives
2
via
an unprecedented cascade reaction in water was constructed. As a result, functionalized quinolizines (
3
) bearing a chromone skeleton were prepared by simple reflux of the mixture of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives in water. Quinolizinium salts (
4
) were also prepared in water under acidic conditions. The formation of quinolizinium salts was accompanied by the formation of two bonds and the cleavage of one bond in a single step. This protocol can be used in the synthesis of a wide variety of quinolizines and quinolizinium salts, and is suitable for combinatorial and parallel syntheses of quinolizine derivatives natural-like products. This approach has several advantages such as the use of an environmentally friendly solvent, simple and practical operation (with filtration and washing without column chromatography separation), excellent yields (83-96%), and formation of a product with potential biological activity.
A protocol for the synthesis of quinolizines from ethyl 2-(pyridine-2-yl)acetates
via
an unprecedented cascade reaction in water was constructed.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/d0gc02460k</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acetic acid ; Biological activity ; Cascade chemical reactions ; Column chromatography ; Combinatorial analysis ; Crystallography ; Derivatives ; Green chemistry ; Pyridines ; Salts ; Synthesis</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2020-10, Vol.22 (2), p.6943-6953</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c344t-2f65615d48ed8bfa7c9aba60c733b93047fa94c2b50ec76e35c839c4d5b5d7cb3</citedby><cites>FETCH-LOGICAL-c344t-2f65615d48ed8bfa7c9aba60c733b93047fa94c2b50ec76e35c839c4d5b5d7cb3</cites><orcidid>0000-0003-2281-1261</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Chen, Li</creatorcontrib><creatorcontrib>Huang, Rong</creatorcontrib><creatorcontrib>Li, Kun</creatorcontrib><creatorcontrib>Yun, Xing-Han</creatorcontrib><creatorcontrib>Yang, Chang-Long</creatorcontrib><creatorcontrib>Yan, Sheng-Jiao</creatorcontrib><title>An environmentally benign cascade reaction of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives for highly site-selective synthesis of quinolizines and quinolizinium salts in water</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>A novel protocol for the synthesis of quinolizines (
3
) and quinolizinium salts (
4
) from chromone-3-carboxaldehydes
1
with ethyl 2-(pyridine-2-yl)acetate derivatives
2
via
an unprecedented cascade reaction in water was constructed. As a result, functionalized quinolizines (
3
) bearing a chromone skeleton were prepared by simple reflux of the mixture of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives in water. Quinolizinium salts (
4
) were also prepared in water under acidic conditions. The formation of quinolizinium salts was accompanied by the formation of two bonds and the cleavage of one bond in a single step. This protocol can be used in the synthesis of a wide variety of quinolizines and quinolizinium salts, and is suitable for combinatorial and parallel syntheses of quinolizine derivatives natural-like products. This approach has several advantages such as the use of an environmentally friendly solvent, simple and practical operation (with filtration and washing without column chromatography separation), excellent yields (83-96%), and formation of a product with potential biological activity.
A protocol for the synthesis of quinolizines from ethyl 2-(pyridine-2-yl)acetates
via
an unprecedented cascade reaction in water was constructed.</description><subject>Acetic acid</subject><subject>Biological activity</subject><subject>Cascade chemical reactions</subject><subject>Column chromatography</subject><subject>Combinatorial analysis</subject><subject>Crystallography</subject><subject>Derivatives</subject><subject>Green chemistry</subject><subject>Pyridines</subject><subject>Salts</subject><subject>Synthesis</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kUFP3DAUhCNUJCj00nslo14oksGJHWdzRNtCK5C40HPkPL9sTL32YnuXpv-R_1Rvt4KeenqjN59mDlMU70t2XjLeXmi2AFYJyX7sFYelkJy2VcPevGhZHRRvY3xgrCwbKQ6L50tH0G1M8G6JLilrJ9KjMwtHQEVQGklABcl4R_xAYAx-6R1STkGF3v9UVuM4aYzkyaSRYBonSyp6upqC0SaDFZ3sJwWYVEKiMZiNSmaT-cEHMprFmAujSUgjWoStReLk0ojRxG3j49o4b82vnBWJcvqfh1kvSVQ2RWIcecr54bjYH5SN-O7vPSq-X325n3-lt3fX3-aXtxS4EIlWg6xlWWsxQz3rB9VAq3olGTSc9y1nohlUK6Dqa4bQSOQ1zHgLQtd9rRvo-VHxcZe7Cv5xjTF1D34dXK7sKlGXs7oRXGbqbEdB8DEGHLpVMEsVpq5k3Xau7jO7nv-Z6ybDH3ZwiPDCvc6Z_ZP_-d1KD_w3Qj-jhw</recordid><startdate>20201021</startdate><enddate>20201021</enddate><creator>Chen, Li</creator><creator>Huang, Rong</creator><creator>Li, Kun</creator><creator>Yun, Xing-Han</creator><creator>Yang, Chang-Long</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/0000-0003-2281-1261</orcidid></search><sort><creationdate>20201021</creationdate><title>An environmentally benign cascade reaction of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives for highly site-selective synthesis of quinolizines and quinolizinium salts in water</title><author>Chen, Li ; Huang, Rong ; Li, Kun ; Yun, Xing-Han ; Yang, Chang-Long ; Yan, Sheng-Jiao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c344t-2f65615d48ed8bfa7c9aba60c733b93047fa94c2b50ec76e35c839c4d5b5d7cb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Acetic acid</topic><topic>Biological activity</topic><topic>Cascade chemical reactions</topic><topic>Column chromatography</topic><topic>Combinatorial analysis</topic><topic>Crystallography</topic><topic>Derivatives</topic><topic>Green chemistry</topic><topic>Pyridines</topic><topic>Salts</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Li</creatorcontrib><creatorcontrib>Huang, Rong</creatorcontrib><creatorcontrib>Li, Kun</creatorcontrib><creatorcontrib>Yun, Xing-Han</creatorcontrib><creatorcontrib>Yang, Chang-Long</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>Chen, Li</au><au>Huang, Rong</au><au>Li, Kun</au><au>Yun, Xing-Han</au><au>Yang, Chang-Long</au><au>Yan, Sheng-Jiao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An environmentally benign cascade reaction of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives for highly site-selective synthesis of quinolizines and quinolizinium salts in water</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2020-10-21</date><risdate>2020</risdate><volume>22</volume><issue>2</issue><spage>6943</spage><epage>6953</epage><pages>6943-6953</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>A novel protocol for the synthesis of quinolizines (
3
) and quinolizinium salts (
4
) from chromone-3-carboxaldehydes
1
with ethyl 2-(pyridine-2-yl)acetate derivatives
2
via
an unprecedented cascade reaction in water was constructed. As a result, functionalized quinolizines (
3
) bearing a chromone skeleton were prepared by simple reflux of the mixture of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives in water. Quinolizinium salts (
4
) were also prepared in water under acidic conditions. The formation of quinolizinium salts was accompanied by the formation of two bonds and the cleavage of one bond in a single step. This protocol can be used in the synthesis of a wide variety of quinolizines and quinolizinium salts, and is suitable for combinatorial and parallel syntheses of quinolizine derivatives natural-like products. This approach has several advantages such as the use of an environmentally friendly solvent, simple and practical operation (with filtration and washing without column chromatography separation), excellent yields (83-96%), and formation of a product with potential biological activity.
A protocol for the synthesis of quinolizines from ethyl 2-(pyridine-2-yl)acetates
via
an unprecedented cascade reaction in water was constructed.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d0gc02460k</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0003-2281-1261</orcidid></addata></record> |
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| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2020-10, Vol.22 (2), p.6943-6953 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_proquest_journals_2451857436 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetic acid Biological activity Cascade chemical reactions Column chromatography Combinatorial analysis Crystallography Derivatives Green chemistry Pyridines Salts Synthesis |
| title | An environmentally benign cascade reaction of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives for highly site-selective synthesis of quinolizines and quinolizinium salts in water |
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