Base‐Catalyzed Cascade Reaction of ortho‐(Propargylamino)aryl Ketones with N‐, O‐, or S‐Based Nucleophiles for the Synthesis of 3‐Functionalized Quinoline Scaffolds
A metal‐free and base‐catalyzed cascade reaction of ortho‐(propargylamino)aryl ketones with primary alcohols, secondary amines, including various N‐heterocycles, and thiols through 1,4‐benzoxazepine intermediates was developed, providing a series of synthetically and medically valuable 3‐functionali...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2018-05, Vol.360 (10), p.1967-1972 |
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| container_end_page | 1972 |
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| container_issue | 10 |
| container_start_page | 1967 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 360 |
| creator | Yu, Liu‐Zhu Wei, Hao‐Zhao Shi, Min |
| description | A metal‐free and base‐catalyzed cascade reaction of ortho‐(propargylamino)aryl ketones with primary alcohols, secondary amines, including various N‐heterocycles, and thiols through 1,4‐benzoxazepine intermediates was developed, providing a series of synthetically and medically valuable 3‐functionalized quinoline derivatives. The reaction process was easily manipulable and environmentally benign, producing 1.0 equiv. of water as the sole byproduct. Furthermore, bimolecular reactions for the synthesis of products containing two quinoline units were also succesful by utilizing this newly developed protocol. |
| doi_str_mv | 10.1002/adsc.201800120 |
| format | Article |
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The reaction process was easily manipulable and environmentally benign, producing 1.0 equiv. of water as the sole byproduct. Furthermore, bimolecular reactions for the synthesis of products containing two quinoline units were also succesful by utilizing this newly developed protocol.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201800120</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>1,4-benzoxazepine ; 3-functionalized quinolines ; Alcohols ; Amines ; Aromatic compounds ; bimolecular reactions ; Cascade chemical reactions ; Chemical synthesis ; Ketones ; metal-free ; Nucleophiles ; ortho-(propargylamino)aryl ketones ; Quinoline ; Thiols</subject><ispartof>Advanced synthesis & catalysis, 2018-05, Vol.360 (10), p.1967-1972</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. 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The reaction process was easily manipulable and environmentally benign, producing 1.0 equiv. of water as the sole byproduct. Furthermore, bimolecular reactions for the synthesis of products containing two quinoline units were also succesful by utilizing this newly developed protocol.</description><subject>1,4-benzoxazepine</subject><subject>3-functionalized quinolines</subject><subject>Alcohols</subject><subject>Amines</subject><subject>Aromatic compounds</subject><subject>bimolecular reactions</subject><subject>Cascade chemical reactions</subject><subject>Chemical synthesis</subject><subject>Ketones</subject><subject>metal-free</subject><subject>Nucleophiles</subject><subject>ortho-(propargylamino)aryl ketones</subject><subject>Quinoline</subject><subject>Thiols</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkctOwzAQRSMEElDYsrbEBiRabCdO0iWEp0C8yj6a-kGDTFzsRCis-AQ-hW_iS5hQBEs2npHmXN_R3CjaYnTEKOX7oIIcccpyShmnS9EaS5kYJiwdL__2gq5G6yE8IpLlWbYWfRxC0J9v7wU0YLtXrUgBQYLS5E6DbCpXE2eI883MIbVz490c_ENn4amq3S74zpIL3bhaB_JSNTNyhdQeuf5-nScTbHoHRa5aabWbzyqLqMFRM9Nk0tVYQhV6kxjZk7b-NgVb9bvctuhiqxpJCcY4q8JGtGLABr35UwfR_cnxfXE2vLw-PS8OLocyFgkdxvk4kQqo4rFR6XSqBJM8MRxULMxUqGme6lQlOjU641wKiWdLOGQJU6kAEQ-i7cW3c--eWx2a8tG1HvcKJUeQ0yylOVKjBSW9C8FrU8599YRXKRkt-1DKPpTyNxQUjBeCF7xD9w9dHhxNij_tF7r2mO8</recordid><startdate>20180516</startdate><enddate>20180516</enddate><creator>Yu, Liu‐Zhu</creator><creator>Wei, Hao‐Zhao</creator><creator>Shi, Min</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20180516</creationdate><title>Base‐Catalyzed Cascade Reaction of ortho‐(Propargylamino)aryl Ketones with N‐, O‐, or S‐Based Nucleophiles for the Synthesis of 3‐Functionalized Quinoline Scaffolds</title><author>Yu, Liu‐Zhu ; Wei, Hao‐Zhao ; Shi, Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3540-3894cda0d23fd6bbd51c24f2ad35fb5db86e6d4e6fe722c5c18042a741d65a53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>1,4-benzoxazepine</topic><topic>3-functionalized quinolines</topic><topic>Alcohols</topic><topic>Amines</topic><topic>Aromatic compounds</topic><topic>bimolecular reactions</topic><topic>Cascade chemical reactions</topic><topic>Chemical synthesis</topic><topic>Ketones</topic><topic>metal-free</topic><topic>Nucleophiles</topic><topic>ortho-(propargylamino)aryl ketones</topic><topic>Quinoline</topic><topic>Thiols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yu, Liu‐Zhu</creatorcontrib><creatorcontrib>Wei, Hao‐Zhao</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yu, Liu‐Zhu</au><au>Wei, Hao‐Zhao</au><au>Shi, Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Base‐Catalyzed Cascade Reaction of ortho‐(Propargylamino)aryl Ketones with N‐, O‐, or S‐Based Nucleophiles for the Synthesis of 3‐Functionalized Quinoline Scaffolds</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2018-05-16</date><risdate>2018</risdate><volume>360</volume><issue>10</issue><spage>1967</spage><epage>1972</epage><pages>1967-1972</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A metal‐free and base‐catalyzed cascade reaction of ortho‐(propargylamino)aryl ketones with primary alcohols, secondary amines, including various N‐heterocycles, and thiols through 1,4‐benzoxazepine intermediates was developed, providing a series of synthetically and medically valuable 3‐functionalized quinoline derivatives. 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| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2018-05, Vol.360 (10), p.1967-1972 |
| issn | 1615-4150 1615-4169 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 1,4-benzoxazepine 3-functionalized quinolines Alcohols Amines Aromatic compounds bimolecular reactions Cascade chemical reactions Chemical synthesis Ketones metal-free Nucleophiles ortho-(propargylamino)aryl ketones Quinoline Thiols |
| title | Base‐Catalyzed Cascade Reaction of ortho‐(Propargylamino)aryl Ketones with N‐, O‐, or S‐Based Nucleophiles for the Synthesis of 3‐Functionalized Quinoline Scaffolds |
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