Calcium-catalyzed formal [3 + 2] annulation of C , N -diacyliminium ions with nucleophilic phenols: a diversity oriented synthesis of 3-aminofurans
We have developed a one-pot, three-component, and solvent-free reaction for the synthesis of 3-aminofurans using a calcium catalyst. In this cascade reaction, the key intermediate, C,N-diacyliminium ion, is formed in situ from glyoxal and lactam, which further reacted with phenolic nucleophiles to f...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2021-02, Vol.19 (5), p.1060-1065 |
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| container_title | Organic & biomolecular chemistry |
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| creator | P, Rajesh Almansour, Abdulrahman I Arumugam, Natarajan Yaragorla, Srinivasarao |
| description | We have developed a one-pot, three-component, and solvent-free reaction for the synthesis of 3-aminofurans using a calcium catalyst. In this cascade reaction, the key intermediate, C,N-diacyliminium ion, is formed in situ from glyoxal and lactam, which further reacted with phenolic nucleophiles to form furan derivatives in good yields with broad substrate diversity. We also present here the preliminary photophysical studies of selected compounds. |
| doi_str_mv | 10.1039/d0ob02276d |
| format | Article |
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In this cascade reaction, the key intermediate, C,N-diacyliminium ion, is formed in situ from glyoxal and lactam, which further reacted with phenolic nucleophiles to form furan derivatives in good yields with broad substrate diversity. 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We also present here the preliminary photophysical studies of selected compounds.</description><subject>Amides</subject><subject>Calcium</subject><subject>Cascade chemical reactions</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Crystallography</subject><subject>Nucleophiles</subject><subject>Phenolic compounds</subject><subject>Phenols</subject><subject>Substrates</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkU1rFTEUhkNR-mU3_gAJuBF19CSZSTLu9FZtodhNuyoy5OaDm5JJrsmMMv0b_mFzbe3C1QmcJ8974EXoOYF3BFj_3kBaA6WCmz10SFohGuhY_-TxTeEAHZVyC0B6wdt9dMBYS7ikcIh-r1TQfh4brSYVljtrsEt5VAHfMPwG0-9YxTgHNfkUcXJ4hd_ib7gxXukl-NHH-hfXXcG__LTBcdbBpu3GB6_xdmNjCuUDVtj4nzYXPy04ZW_jVGPKEqeNLb7stKxR1ZXcnFUsz9BTp0KxJw_zGF1_-Xy1OmsuLr-erz5eNJq23dQQ6KR13FjGO-eEMVYa0pGWcuKo6EESyjsuobO81T0hBNYSjBTQU-MkIewYvbr3bnP6MdsyDaMv2oagok1zGWgrqoD1rajoy__Q2zTnWK-rlKwZNWwnfH1P6ZxKydYN2-xHlZeBwLCrajiFy09_qzqt8IsH5bwerXlE_3XD_gBH2o2Y</recordid><startdate>20210211</startdate><enddate>20210211</enddate><creator>P, Rajesh</creator><creator>Almansour, Abdulrahman I</creator><creator>Arumugam, Natarajan</creator><creator>Yaragorla, Srinivasarao</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6152-5861</orcidid></search><sort><creationdate>20210211</creationdate><title>Calcium-catalyzed formal [3 + 2] annulation of C , N -diacyliminium ions with nucleophilic phenols: a diversity oriented synthesis of 3-aminofurans</title><author>P, Rajesh ; Almansour, Abdulrahman I ; Arumugam, Natarajan ; Yaragorla, Srinivasarao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c245t-1058ef6de365ff7dde8d1514261f2790812656805e64c91110b80d87092df8113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amides</topic><topic>Calcium</topic><topic>Cascade chemical reactions</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Crystallography</topic><topic>Nucleophiles</topic><topic>Phenolic compounds</topic><topic>Phenols</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>P, Rajesh</creatorcontrib><creatorcontrib>Almansour, Abdulrahman I</creatorcontrib><creatorcontrib>Arumugam, Natarajan</creatorcontrib><creatorcontrib>Yaragorla, Srinivasarao</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>P, Rajesh</au><au>Almansour, Abdulrahman I</au><au>Arumugam, Natarajan</au><au>Yaragorla, Srinivasarao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Calcium-catalyzed formal [3 + 2] annulation of C , N -diacyliminium ions with nucleophilic phenols: a diversity oriented synthesis of 3-aminofurans</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2021-02-11</date><risdate>2021</risdate><volume>19</volume><issue>5</issue><spage>1060</spage><epage>1065</epage><pages>1060-1065</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>We have developed a one-pot, three-component, and solvent-free reaction for the synthesis of 3-aminofurans using a calcium catalyst. 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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2021-02, Vol.19 (5), p.1060-1065 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amides Calcium Cascade chemical reactions Catalysts Chemical reactions Chemical synthesis Crystallography Nucleophiles Phenolic compounds Phenols Substrates |
| title | Calcium-catalyzed formal [3 + 2] annulation of C , N -diacyliminium ions with nucleophilic phenols: a diversity oriented synthesis of 3-aminofurans |
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