Ammonia synthons for the multicomponent assembly of complex γ-lactams
The synthesis of γ-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N-functionalization is reported. A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a su...
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| Veröffentlicht in: | Proceedings of the National Academy of Sciences - PNAS 2011, Vol.108 (17), p.6781-6786 |
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| container_title | Proceedings of the National Academy of Sciences - PNAS |
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| creator | Tan, Darlene Q Martin, Kevin S Fettinger, James C Shaw, Jared T |
| description | The synthesis of γ-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N-functionalization is reported. A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a subsequent synthetic step. These methods represent the first multicomponent assembly of complex lactam structures that are unsubstituted at nitrogen. In addition, two methods for the introduction of nitrogen substituents that are not possible through the original 4CR are reported. X-ray crystallographic analysis of representative structures reveals conformational changes in the core structure that will enable future deployment of this chemistry in the design and synthesis of diverse collections of lactams suitable for the discovery of new biological probes. |
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A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a subsequent synthetic step. These methods represent the first multicomponent assembly of complex lactam structures that are unsubstituted at nitrogen. In addition, two methods for the introduction of nitrogen substituents that are not possible through the original 4CR are reported. X-ray crystallographic analysis of representative structures reveals conformational changes in the core structure that will enable future deployment of this chemistry in the design and synthesis of diverse collections of lactams suitable for the discovery of new biological probes.</description><identifier>ISSN: 0027-8424</identifier><identifier>EISSN: 1091-6490</identifier><language>eng</language><publisher>National Academy of Sciences</publisher><subject>ammonia ; chemistry ; lactams ; nitrogen ; X-ray diffraction</subject><ispartof>Proceedings of the National Academy of Sciences - PNAS, 2011, Vol.108 (17), p.6781-6786</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,4012</link.rule.ids></links><search><creatorcontrib>Tan, Darlene Q</creatorcontrib><creatorcontrib>Martin, Kevin S</creatorcontrib><creatorcontrib>Fettinger, James C</creatorcontrib><creatorcontrib>Shaw, Jared T</creatorcontrib><title>Ammonia synthons for the multicomponent assembly of complex γ-lactams</title><title>Proceedings of the National Academy of Sciences - PNAS</title><description>The synthesis of γ-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N-functionalization is reported. 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X-ray crystallographic analysis of representative structures reveals conformational changes in the core structure that will enable future deployment of this chemistry in the design and synthesis of diverse collections of lactams suitable for the discovery of new biological probes.</description><subject>ammonia</subject><subject>chemistry</subject><subject>lactams</subject><subject>nitrogen</subject><subject>X-ray diffraction</subject><issn>0027-8424</issn><issn>1091-6490</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFyksKwjAUQNEgCtbPGswGAi9pbZuhiOJcHZdYElvJR_oi2E24GXegGxPBuaMLhzsgCQfJWZ5JGJIEQBSszEQ2JhPECwDIZQkJ2a2cC75VFHsfm-CRmtDR2Gjqbja2dXDX4LWPVCFqd7I9DYZ-1eo7fT9eT2ZVHZXDGRkZZVHPf52SxXZzWO-YUaFS567F6rgXwHMALoUo0vT_8QHGiDnf</recordid><startdate>2011</startdate><enddate>2011</enddate><creator>Tan, Darlene Q</creator><creator>Martin, Kevin S</creator><creator>Fettinger, James C</creator><creator>Shaw, Jared T</creator><general>National Academy of Sciences</general><scope>FBQ</scope></search><sort><creationdate>2011</creationdate><title>Ammonia synthons for the multicomponent assembly of complex γ-lactams</title><author>Tan, Darlene Q ; Martin, Kevin S ; Fettinger, James C ; Shaw, Jared T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-fao_agris_US2016001922733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>ammonia</topic><topic>chemistry</topic><topic>lactams</topic><topic>nitrogen</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tan, Darlene Q</creatorcontrib><creatorcontrib>Martin, Kevin S</creatorcontrib><creatorcontrib>Fettinger, James C</creatorcontrib><creatorcontrib>Shaw, Jared T</creatorcontrib><collection>AGRIS</collection><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tan, Darlene Q</au><au>Martin, Kevin S</au><au>Fettinger, James C</au><au>Shaw, Jared T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ammonia synthons for the multicomponent assembly of complex γ-lactams</atitle><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle><date>2011</date><risdate>2011</risdate><volume>108</volume><issue>17</issue><spage>6781</spage><epage>6786</epage><pages>6781-6786</pages><issn>0027-8424</issn><eissn>1091-6490</eissn><abstract>The synthesis of γ-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N-functionalization is reported. A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a subsequent synthetic step. These methods represent the first multicomponent assembly of complex lactam structures that are unsubstituted at nitrogen. In addition, two methods for the introduction of nitrogen substituents that are not possible through the original 4CR are reported. X-ray crystallographic analysis of representative structures reveals conformational changes in the core structure that will enable future deployment of this chemistry in the design and synthesis of diverse collections of lactams suitable for the discovery of new biological probes.</abstract><pub>National Academy of Sciences</pub></addata></record> |
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| ispartof | Proceedings of the National Academy of Sciences - PNAS, 2011, Vol.108 (17), p.6781-6786 |
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| source | Jstor Complete Legacy; PubMed Central; Alma/SFX Local Collection; Free Full-Text Journals in Chemistry |
| subjects | ammonia chemistry lactams nitrogen X-ray diffraction |
| title | Ammonia synthons for the multicomponent assembly of complex γ-lactams |
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