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Concise synthesis of α-substituted 2-benzofuranmethamines and other 2-substituted benzofurans via α-substituted 2-benzofuranmethyl carbocation intermediates

Wongsa, Nikhom; Sommart, Ubonta; Ritthiwigrom, Thunwadee; Yazici, Arife; Kanokmedhakul, Somdej; Kanokmedhakul, Kwanjai; Willis, Anthony; Pyne, Stephen G

Description

Propargyl 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...[Show more]

CollectionsANU Research Publications
Date published: 2013
Type: Journal article
URI: http://hdl.handle.net/1885/70777
Source: Journal of Organic Chemistry
DOI: 10.1021/jo302554v

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