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Tandem Reaction of Arynes with Tertiary Amines and Aldehydes: Formation of 9‐ and 10‐Membered Dibenzo[1,5]oxaza Heterocycles
Author(s) -
Okuma Kentaro,
Kinoshita Hiroaki,
Nagahora Noriyoshi,
Shioji Kosei
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600244
Subject(s) - aryne , chemistry , trimethylsilyl , trifluoromethanesulfonate , benzaldehyde , intramolecular force , medicinal chemistry , cascade reaction , yield (engineering) , nucleophilic substitution , ether , tandem , nucleophile , organic chemistry , catalysis , materials science , metallurgy , composite material
The aryne‐mediated three‐component reaction of arynes, tertiary amines, and aldehydes followed by intramolecular nucleophilic aromatic substitution afforded novel 9‐ and 10‐membered heterocycles. Thus, the reaction of 2‐(trimethylsilyl)phenyl triflate with N ‐phenylmorpholine and benzaldehyde in the presence of CsF gave o ‐morpholinobenzhydryl phenyl ether in 76 % yield. By using N ‐methylindoline, nine‐membered dibenzo[1,5]oxazonines were synthesized in moderate yields.