Please use this identifier to cite or link to this item:
Full metadata record
DC FieldValueLanguage
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.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.titleConcise synthesis of α-substituted 2-benzofuranmethamines and other 2-subsituted benzofurans via α-substituted 2-benzofuranmethyl carbocation intermediatesen_US
article.title.sourcetitleJournal of Organic Chemistryen_US
article.volume78en_US of Wollongongen_US Kaen Universityen_US of Songkla Universityen_US National Universityen_US Mai Universityen_US
Appears in Collections:CMUL: Journal Articles

Files in This Item:
There are no files associated with this item.

Items in CMUIR are protected by copyright, with all rights reserved, unless otherwise indicated.