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dc.contributor.authorChen, Chih-Hauen_US
dc.contributor.authorKuo, Jarenen_US
dc.contributor.authorYellol, Gorakh S.en_US
dc.contributor.authorSun, Chung-Mingen_US
dc.date.accessioned2014-12-08T15:32:25Z-
dc.date.available2014-12-08T15:32:25Z-
dc.date.issued2011-06-06en_US
dc.identifier.issn1861-4728en_US
dc.identifier.urihttp://dx.doi.org/10.1002/asia.201000913en_US
dc.identifier.urihttp://hdl.handle.net/11536/22758-
dc.description.abstractA novel strategy for an unconventional Pictet-Spengler reaction has been developed for the regioselective cyclization of the imidazole ring system at the C2 position. The developed strategy was utilized to develop a diversity-oriented parallel synthesis for bis(heterocyclic) skeletal novel analogs of benzimidazole-linked imidazoquinoxalines on a soluble polymer support under microwave conditions. Condensation of polymer-immobilized o-phenylenediamines with 4-fluoro-3-nitrobenzoic acid followed by nucleophilic aromatic substitution with an imidazole motif affords bis(heterocyclic) skeletal precursors for the Pictet-Spengler reaction. The unconventional Pictet-Spengler cyclization with various aldehydes was achieved regioselectively at the C2 position of the imidazole ring to furnish rare imidazole-fused quinoxaline skeletons. During the Pictet-Spengler cyclization, aldehydes bearing electron-donating groups afford 4,5-dihydro-imidazoquinoxalines, which then auto-aromatize into benzimidazole-linked imidazo[1,2-a]quinoxalines. However, interestingly, aldehydes bearing electron-withdrawing groups directly provide aromatized imidazo[1,2-a]quinoxalines, which unexpectedly afford novel benzimidazole-linked 4-methoxy-4,5-dihydro-imidazo[1,2-a] quinoxalines after polymer cleavage.en_US
dc.language.isoen_USen_US
dc.subjectdiversity-oriented synthesisen_US
dc.subjectheterocyclesen_US
dc.subjectmicrowave chemistryen_US
dc.subjectPictet-Spengler cyclizationen_US
dc.subjectsolid-phase synthesisen_US
dc.titleRegioselective, Unconventional Pictet-Spengler Cyclization Strategy Toward the Synthesis of Benzimidazole-Linked Imidazoquinoxalines on a Soluble Polymer Supporten_US
dc.typeArticleen_US
dc.identifier.doi10.1002/asia.201000913en_US
dc.identifier.journalCHEMISTRY-AN ASIAN JOURNALen_US
dc.citation.volume6en_US
dc.citation.issue6en_US
dc.citation.spage1557en_US
dc.citation.epage1565en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000292097700038-
dc.citation.woscount4-
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