Synthesis of on resin poly(propylene imine) dendrimer and its use as organocatalyst
Solid phase synthesis of poly(propylene imine) dendrimer is described. An iterative synthesis including double Michael addition of acrylonitrile to the primary amino groups on crosslinked polystyrene support followed by reduction of nitrile groups to amino groups give poly(propylene imine) dendrimer...
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| Veröffentlicht in: | Tetrahedron letters 2014-04, Vol.55 (15), p.2352-2354 |
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| creator | Gopalakrishna Panicker, Rajesh Krishnan Krishnapillai, Sreekumar |
| description | Solid phase synthesis of poly(propylene imine) dendrimer is described. An iterative synthesis including double Michael addition of acrylonitrile to the primary amino groups on crosslinked polystyrene support followed by reduction of nitrile groups to amino groups give poly(propylene imine) dendrimers up to third generation attached to the polystyrene support. The supported dendrimer is used as an organocatalyst to Knoevenagel condensations. The supported catalyst showed good selectivity and the product was obtained in excellent yield under green reaction conditions. Densely packed amino groups enhance catalysis by a co-operative effect. The catalyst is recoverable and reusable. |
| doi_str_mv | 10.1016/j.tetlet.2014.02.084 |
| format | Article |
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An iterative synthesis including double Michael addition of acrylonitrile to the primary amino groups on crosslinked polystyrene support followed by reduction of nitrile groups to amino groups give poly(propylene imine) dendrimers up to third generation attached to the polystyrene support. The supported dendrimer is used as an organocatalyst to Knoevenagel condensations. The supported catalyst showed good selectivity and the product was obtained in excellent yield under green reaction conditions. Densely packed amino groups enhance catalysis by a co-operative effect. 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An iterative synthesis including double Michael addition of acrylonitrile to the primary amino groups on crosslinked polystyrene support followed by reduction of nitrile groups to amino groups give poly(propylene imine) dendrimers up to third generation attached to the polystyrene support. The supported dendrimer is used as an organocatalyst to Knoevenagel condensations. The supported catalyst showed good selectivity and the product was obtained in excellent yield under green reaction conditions. Densely packed amino groups enhance catalysis by a co-operative effect. The catalyst is recoverable and reusable.</description><subject>Acrylonitriles</subject><subject>Catalysts</subject><subject>Dendrimer</subject><subject>Dendrimers</subject><subject>Imines</subject><subject>Knoevenagel condensation</subject><subject>Organocatalysis</subject><subject>Poly(propylene imine)</subject><subject>Polymers</subject><subject>Polystyrene resins</subject><subject>Solid phase synthesis</subject><subject>Synthesis (chemistry)</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kDtPAzEQhC0EEiHwDyhchuKO9SP3aJAQ4iVFogjUlmPvgaOLL9gO0v17HB012-wWM6Odj5BrBiUDVt1uy4Spx1RyYLIEXkIjT8iMNbUoxLJhp2QGIKGQINpzchHjFvJUDczIej369IXRRTp0dPA05NvT_dCPi30Y9mOPHqnbOY831KK3we0wUO0tdSnSQ0SqszV8aj8YnXQ_xnRJzjrdR7z623Py8fT4_vBSrN6eXx_uV4URok0Fr-1GtKJeCrnBpgIpLegWunqpl2CFwU7UTbupkKPQlvMud6hNW0nkzPJNJeZkMeXmR78PGJPauWiw77XH4RAVq6Wsmpbzo1ROUhOGGAN2ap-L6DAqBurIUG3VxFAdGSrgKjPMtrvJhrnGj8OgonHoDVoX0CRlB_d_wC9yz3zZ</recordid><startdate>20140409</startdate><enddate>20140409</enddate><creator>Gopalakrishna Panicker, Rajesh Krishnan</creator><creator>Krishnapillai, Sreekumar</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20140409</creationdate><title>Synthesis of on resin poly(propylene imine) dendrimer and its use as organocatalyst</title><author>Gopalakrishna Panicker, Rajesh Krishnan ; Krishnapillai, Sreekumar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c339t-27db3937534be86044d0a90f75a50d3cef3789b6e2e3ad22f0047c964e21d2b63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Acrylonitriles</topic><topic>Catalysts</topic><topic>Dendrimer</topic><topic>Dendrimers</topic><topic>Imines</topic><topic>Knoevenagel condensation</topic><topic>Organocatalysis</topic><topic>Poly(propylene imine)</topic><topic>Polymers</topic><topic>Polystyrene resins</topic><topic>Solid phase synthesis</topic><topic>Synthesis (chemistry)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gopalakrishna Panicker, Rajesh Krishnan</creatorcontrib><creatorcontrib>Krishnapillai, Sreekumar</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gopalakrishna Panicker, Rajesh Krishnan</au><au>Krishnapillai, Sreekumar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of on resin poly(propylene imine) dendrimer and its use as organocatalyst</atitle><jtitle>Tetrahedron letters</jtitle><date>2014-04-09</date><risdate>2014</risdate><volume>55</volume><issue>15</issue><spage>2352</spage><epage>2354</epage><pages>2352-2354</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>Solid phase synthesis of poly(propylene imine) dendrimer is described. An iterative synthesis including double Michael addition of acrylonitrile to the primary amino groups on crosslinked polystyrene support followed by reduction of nitrile groups to amino groups give poly(propylene imine) dendrimers up to third generation attached to the polystyrene support. The supported dendrimer is used as an organocatalyst to Knoevenagel condensations. The supported catalyst showed good selectivity and the product was obtained in excellent yield under green reaction conditions. Densely packed amino groups enhance catalysis by a co-operative effect. The catalyst is recoverable and reusable.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2014.02.084</doi><tpages>3</tpages></addata></record> |
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| ispartof | Tetrahedron letters, 2014-04, Vol.55 (15), p.2352-2354 |
| issn | 0040-4039 1873-3581 |
| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Acrylonitriles Catalysts Dendrimer Dendrimers Imines Knoevenagel condensation Organocatalysis Poly(propylene imine) Polymers Polystyrene resins Solid phase synthesis Synthesis (chemistry) |
| title | Synthesis of on resin poly(propylene imine) dendrimer and its use as organocatalyst |
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