Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl3‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates
A strategy has been established for the synthesis of 2,4‐diaryl‐1,3‐benzoxazines via a FeCl3‐catalyzed annulation of ortho‐hydroxyphenyl‐substituted para‐quinone methides (p‐QMs) and imidates. This transformation proceeds under mild, operationally‐simple conditions in a very short time. A wide range...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2019-10, Vol.361 (20), p.4811-4816 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Zhang, Jing‐Ru Jin, Hai‐Shan Wang, Ru‐Bing Zhao, Li‐Ming |
| description | A strategy has been established for the synthesis of 2,4‐diaryl‐1,3‐benzoxazines via a FeCl3‐catalyzed annulation of ortho‐hydroxyphenyl‐substituted para‐quinone methides (p‐QMs) and imidates. This transformation proceeds under mild, operationally‐simple conditions in a very short time. A wide range of substrates was accessed in this facile chemical transformation, in which the cyclized products were isolated in good to excellent yields (37% to 98%). This reaction not only provides an efficient method for the construction of biologically important 2,4‐diaryl‐1,3‐benzoxazines but also greatly enriches the chemistry of p‐QMs. |
| doi_str_mv | 10.1002/adsc.201900842 |
| format | Article |
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This transformation proceeds under mild, operationally‐simple conditions in a very short time. A wide range of substrates was accessed in this facile chemical transformation, in which the cyclized products were isolated in good to excellent yields (37% to 98%). This reaction not only provides an efficient method for the construction of biologically important 2,4‐diaryl‐1,3‐benzoxazines but also greatly enriches the chemistry of p‐QMs.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201900842</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>1,3-benzoxazines ; 1,6-conjugated addition ; annulation ; Benzoxazines ; Chemical reactions ; Ferric chloride ; iron ; Iron chlorides ; Organic chemistry ; para-quinone methides ; Quinones ; Substitutes ; Substrates ; Transformations</subject><ispartof>Advanced synthesis & catalysis, 2019-10, Vol.361 (20), p.4811-4816</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. 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This transformation proceeds under mild, operationally‐simple conditions in a very short time. A wide range of substrates was accessed in this facile chemical transformation, in which the cyclized products were isolated in good to excellent yields (37% to 98%). This reaction not only provides an efficient method for the construction of biologically important 2,4‐diaryl‐1,3‐benzoxazines but also greatly enriches the chemistry of p‐QMs.</description><subject>1,3-benzoxazines</subject><subject>1,6-conjugated addition</subject><subject>annulation</subject><subject>Benzoxazines</subject><subject>Chemical reactions</subject><subject>Ferric chloride</subject><subject>iron</subject><subject>Iron chlorides</subject><subject>Organic chemistry</subject><subject>para-quinone methides</subject><subject>Quinones</subject><subject>Substitutes</subject><subject>Substrates</subject><subject>Transformations</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNo9UMtOwzAQjBBIlMKVcySubbHXeflYpZRWKkKocI6cxCGuUjvEDm164hP4AL6OL8EB1Mu-ZnZWO45zjdEEIwS3LNfZBBCmCEUenDgDHGB_7OGAnh5rH507F1pvEMJhFIYD52vdSVNyLbSrChdG3vfH50ywpqtsgUfExpTLg9qzg5Bcu--CuXMeVz0QM8Oq7sBzdyplWzEjlOxVVGNKZfFFlzdq39Ull79y6zbVRpjW2I2aNcyOnlohleTuAzelyK3-TpjSXW5FzgzXl85ZwSrNr_7z0HmZ3z3Hi_Hq8X4ZT1fjVwgRjDHQICM-TTEB6kPG7GsUfAwFQUGaFwxjCpgGEEUQoDTLfOBZigLOCuoRGpKhc_OnWzfqreXaJBvVNtKeTICg0POARGBZ9I-1ExXvkroRW-tTglHS25_09idH-5PpbB0fO_IDpImDwA</recordid><startdate>20191022</startdate><enddate>20191022</enddate><creator>Zhang, Jing‐Ru</creator><creator>Jin, Hai‐Shan</creator><creator>Wang, Ru‐Bing</creator><creator>Zhao, Li‐Ming</creator><general>Wiley Subscription Services, Inc</general><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20191022</creationdate><title>Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl3‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates</title><author>Zhang, Jing‐Ru ; Jin, Hai‐Shan ; Wang, Ru‐Bing ; Zhao, Li‐Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g2702-1296c359b132952ca78792512f306bdfa1192196288260bcc52ecb06eaf943973</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>1,3-benzoxazines</topic><topic>1,6-conjugated addition</topic><topic>annulation</topic><topic>Benzoxazines</topic><topic>Chemical reactions</topic><topic>Ferric chloride</topic><topic>iron</topic><topic>Iron chlorides</topic><topic>Organic chemistry</topic><topic>para-quinone methides</topic><topic>Quinones</topic><topic>Substitutes</topic><topic>Substrates</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Jing‐Ru</creatorcontrib><creatorcontrib>Jin, Hai‐Shan</creatorcontrib><creatorcontrib>Wang, Ru‐Bing</creatorcontrib><creatorcontrib>Zhao, Li‐Ming</creatorcontrib><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>Zhang, Jing‐Ru</au><au>Jin, Hai‐Shan</au><au>Wang, Ru‐Bing</au><au>Zhao, Li‐Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl3‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2019-10-22</date><risdate>2019</risdate><volume>361</volume><issue>20</issue><spage>4811</spage><epage>4816</epage><pages>4811-4816</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A strategy has been established for the synthesis of 2,4‐diaryl‐1,3‐benzoxazines via a FeCl3‐catalyzed annulation of ortho‐hydroxyphenyl‐substituted para‐quinone methides (p‐QMs) and imidates. This transformation proceeds under mild, operationally‐simple conditions in a very short time. A wide range of substrates was accessed in this facile chemical transformation, in which the cyclized products were isolated in good to excellent yields (37% to 98%). This reaction not only provides an efficient method for the construction of biologically important 2,4‐diaryl‐1,3‐benzoxazines but also greatly enriches the chemistry of p‐QMs.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201900842</doi><tpages>6</tpages></addata></record> |
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| subjects | 1,3-benzoxazines 1,6-conjugated addition annulation Benzoxazines Chemical reactions Ferric chloride iron Iron chlorides Organic chemistry para-quinone methides Quinones Substitutes Substrates Transformations |
| title | Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl3‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates |
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