Facile synthesis of regio-isomeric naphthofurans and benzodifurans

Naphtho[1,2- b]furans 1a– f , naphtho[2,1- b]furans 2a– f , benzo[1,2- b:5,4- b′]difurans 3a– b , benzo[1,2- b:4,5- b′]difurans 4a– b , and benzo[1,2- b:4,3- b′]difurans 5a– b were synthesized by base-catalyzed cyclization reaction of the corresponding o-alkoxybenzoylarene derivatives. The o-alkoxyb...

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Bibliographic Details
Published in:Tetrahedron 2005-01, Vol.61 (3), p.545-553
Main Authors: Park, Kwanghee Koh, Jeong, Jinsuk
Format: Article
Language:English
Subjects:
Benzo[1,2- b:4,3- b′]difuran
Benzo[1,2- b:4,5- b′]difuran
Benzo[1,2- b:5,4- b′]difuran
Naphtho[1,2- b]furan
Naphtho[2,1- b]furan
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Summary:Naphtho[1,2- b]furans 1a– f , naphtho[2,1- b]furans 2a– f , benzo[1,2- b:5,4- b′]difurans 3a– b , benzo[1,2- b:4,5- b′]difurans 4a– b , and benzo[1,2- b:4,3- b′]difurans 5a– b were synthesized by base-catalyzed cyclization reaction of the corresponding o-alkoxybenzoylarene derivatives. The o-alkoxybenzoylarenes were obtained from the etherification reaction of the o-hydroxybenzoylarenes, which were prepared either by the reaction of methoxyarenes with benzoyl chloride in the presence of aluminum chloride or by photo-Fries rearrangement of aryl benzoates. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.11.022