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HFIP‐Mediated Decarboxylative [4+3]‐Annulation of Azaoxyallyl Cations with Isatoic Anhydride
Author(s) -
Kim Eunjin,
Lee Chang Yoon,
Kim SungGon
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000439
Subject(s) - annulation , chemistry , yield (engineering) , intramolecular force , cascade , cascade reaction , organic chemistry , medicinal chemistry , catalysis , materials science , chromatography , metallurgy
The first example of a [4+3]‐annulation reaction between in situ‐generated azaoxyallyl cations and isatoic anhydride has been developed for the construction of seven‐membered 1,4‐benzodiazepinediones in moderate to good yields (up to 91% yield). This annulation reaction involves the cascade reaction of decarboxylative addition of hexafluoroisopropanol to isatoic anhydride, addition to the azaoxyallyl cation, and intramolecular substitution to yield 1,4‐benzodiazepinediones.