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Aryne Cycloaddition with Stable Münchnones: Synthesis of 9,10‐Dihydro‐9,10‐epiminoanthracenes and Isoindoles
Author(s) -
Fang Yuesi,
Larock Richard C.,
Shi Feng
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300221
Subject(s) - aryne , isoindole , cycloaddition , chemistry , mesoionic , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
Arynes react with stable münchnones in a [3+2] cycloaddition/[4+2] cycloreversion sequence under mild conditions. The reaction initially affords isoindoles, but in the presence of excess arynes, these isoindole intermediates readily undergo a further aryne [4+2] cycloaddition to afford 9,10‐dihydro‐9,10‐epiminoanthracenes in good to excellent yields. Controlling the reaction conditions to stop at the isoindole stage was attempted but proved difficult and limited. This chemistry further expands aryne dipolar cycloaddition chemistry with mesoionic substrates.