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