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dc.contributor.authorNikhom Wongsaen_US
dc.contributor.authorUbonta Sommarten_US
dc.contributor.authorThunwadee Ritthiwigromen_US
dc.contributor.authorArife Yazicien_US
dc.contributor.authorSomdej Kanokmedhakulen_US
dc.contributor.authorKwanjai Kanokmedhakulen_US
dc.contributor.authorAnthony C. Willisen_US
dc.contributor.authorStephen G. Pyneen_US
dc.date.accessioned2018-09-04T09:24:52Z-
dc.date.available2018-09-04T09:24:52Z-
dc.date.issued2013-02-01en_US
dc.identifier.issn15206904en_US
dc.identifier.issn00223263en_US
dc.identifier.other2-s2.0-84873325933en_US
dc.identifier.other10.1021/jo302554ven_US
dc.identifier.urihttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84873325933&origin=inwarden_US
dc.identifier.urihttp://cmuir.cmu.ac.th/jspui/handle/6653943832/52406-
dc.description.abstractPropargyl amines 4, where R3 is aryl, undergo 5-exo-dig cyclization reactions under relatively mild conditions (AgNO3, DMF, 60 C, 1 h) to give 3-amino-2,3-dihydro-2-arylmethylidenebenzofurans 5 (R 3 = aryl). In contrast, substrates where R3 is alkyl undergo competing 6-endo-dig and 5-exo-dig cyclization processes. The hydroxymethyl substrate 4 (R3 = CH2OH), however, was smoothly converted to its corresponding 5-exo-dig cyclization product 5, likely due to the assistance of the primary hydroxyl group in the 5-exo-dig cyclization process by silver cation coordination. Under more enforcing conditions (AgNO3, DMF, 100 C, 18 h), the initially formed products 5 undergo a 1,3-allylic rearrangement to their corresponding 2-substituted benzofuran derivatives 6. This rearrangement can also be effected by treating 5 with AgNO3 in DMF at 100 C for 18 h or BF3·Et 2O at rt. 2-(3-Butenyl)benzofurans 7 (Nu = allyl) can be prepared by treatment of 5 with BF3·Et2O and allyltributylstannane. Furan and MeOH could also be employed as external nucleophiles in these BF3·Et2O-promoted reactions. © 2013 American Chemical Society.en_US
dc.subjectChemistryen_US
dc.titleConcise synthesis of α-substituted 2-benzofuranmethamines and other 2-subsituted benzofurans via α-substituted 2-benzofuranmethyl carbocation intermediatesen_US
dc.typeJournalen_US
article.title.sourcetitleJournal of Organic Chemistryen_US
article.volume78en_US
article.stream.affiliationsUniversity of Wollongongen_US
article.stream.affiliationsKhon Kaen Universityen_US
article.stream.affiliationsPrince of Songkla Universityen_US
article.stream.affiliationsAustralian National Universityen_US
article.stream.affiliationsChiang Mai Universityen_US
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