Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs) Based on Staudinger and Passerini Three-Component Reactions
Multiple multicomponent macrocyclizations including bifunctional buildings blocks (MiBs) so far have relied almost exclusively on Ugi reactions. The efficient expansion to non-Ugi-MiBs is exemplified by the synthesis of tetra-β-lactam and bis-α-acyloxy carboxamide macrocycles based on multiple Staud...
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Veröffentlicht in: | Journal of organic chemistry 2008-03, Vol.73 (5), p.1762-1767 |
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container_title | Journal of organic chemistry |
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creator | Leon, Fredy Rivera, Daniel G Wessjohann, Ludger A |
description | Multiple multicomponent macrocyclizations including bifunctional buildings blocks (MiBs) so far have relied almost exclusively on Ugi reactions. The efficient expansion to non-Ugi-MiBs is exemplified by the synthesis of tetra-β-lactam and bis-α-acyloxy carboxamide macrocycles based on multiple Staudinger and Passerini three-component reactions (3CR), respectively. A recent variation of the Passerini-3CR that involves primary alcohols, isocyanides, and carboxylic acids under oxidative conditions is successfully adapted to this procedure. |
doi_str_mv | 10.1021/jo7022125 |
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Org. Chem</addtitle><description>Multiple multicomponent macrocyclizations including bifunctional buildings blocks (MiBs) so far have relied almost exclusively on Ugi reactions. The efficient expansion to non-Ugi-MiBs is exemplified by the synthesis of tetra-β-lactam and bis-α-acyloxy carboxamide macrocycles based on multiple Staudinger and Passerini three-component reactions (3CR), respectively. A recent variation of the Passerini-3CR that involves primary alcohols, isocyanides, and carboxylic acids under oxidative conditions is successfully adapted to this procedure.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Macrocyclic Compounds - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Spectrometry, Mass, Electrospray Ionization - methods</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkcFu1DAQhi0EokvhwAsgX0D0ELCdOE6OzQpopa4odJG4WbPeCbj1OosnkSivwQuT7K62F3yx9fvz59EMYy-leCeFku9vOyOUkko_YjOplcjKWhSP2UyMaZarMj9hz4huxbi01k_ZiaxUYYqqnrG_iyH0fhuQ7w6u22y7iLHnC3Cpc_cu-D_Q-y4Sv4wuDGsff_DGt0N0UwqBN4MP-zR07o7424Vv6Iw3QLjmXeQ3PexeYeIQ1_waiDD56PnyZ0LM5scfvyLsnPScPWkhEL447Kfs28cPy_lFdvX50-X8_CqDojB9ppTTULVaagTpCiNqhQArxByxNrVzdV0aIyujXZGbQlRCtaIqS70CtW5zk5-yN3vvNnW_BqTebjw5DAEidgNZI_LJOoFne3BsCVHC1m6T30C6t1LYaQL2OIGRfXWQDqsNrh_IQ8tH4PUBAHIQ2gTReTpySshKq2ISZXvOU4-_j_eQ7mxpcqPt8vrGVkX5vbn40tjlgxccjfUMaRwO_afAfyFyqpU</recordid><startdate>20080307</startdate><enddate>20080307</enddate><creator>Leon, Fredy</creator><creator>Rivera, Daniel G</creator><creator>Wessjohann, Ludger A</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080307</creationdate><title>Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs) Based on Staudinger and Passerini Three-Component Reactions</title><author>Leon, Fredy ; Rivera, Daniel G ; Wessjohann, Ludger A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-22c5a8f515ea1c47092eaabee3ee979cc996771875c43740802f08665ba2df373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Macrocyclic Compounds - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Spectrometry, Mass, Electrospray Ionization - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leon, Fredy</creatorcontrib><creatorcontrib>Rivera, Daniel G</creatorcontrib><creatorcontrib>Wessjohann, Ludger A</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Leon, Fredy</au><au>Rivera, Daniel G</au><au>Wessjohann, Ludger A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs) Based on Staudinger and Passerini Three-Component Reactions</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-03-07</date><risdate>2008</risdate><volume>73</volume><issue>5</issue><spage>1762</spage><epage>1767</epage><pages>1762-1767</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Multiple multicomponent macrocyclizations including bifunctional buildings blocks (MiBs) so far have relied almost exclusively on Ugi reactions. The efficient expansion to non-Ugi-MiBs is exemplified by the synthesis of tetra-β-lactam and bis-α-acyloxy carboxamide macrocycles based on multiple Staudinger and Passerini three-component reactions (3CR), respectively. A recent variation of the Passerini-3CR that involves primary alcohols, isocyanides, and carboxylic acids under oxidative conditions is successfully adapted to this procedure.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18247489</pmid><doi>10.1021/jo7022125</doi><tpages>6</tpages></addata></record> |
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subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Macrocyclic Compounds - chemistry Magnetic Resonance Spectroscopy Organic chemistry Preparations and properties Spectrometry, Mass, Electrospray Ionization - methods |
title | Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs) Based on Staudinger and Passerini Three-Component Reactions |
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