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[8+3]‐Cycloaddition of Tropones with Azaoxyallyl Cations
Author(s) -
Roy Tony,
Jacob Anu,
Bhattacharjee Subrata,
Biju Akkattu T.
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901198
Subject(s) - cycloaddition , chemistry , catalysis , nitrogen , transition metal , photochemistry , carbon fibers , cycloheptatriene , medicinal chemistry , organic chemistry , materials science , composite number , composite material
Although azaoxyallyl cations are widely used as 1,3‐dipoles for various cycloaddition reactions leading to nitrogen‐containing heterocycles, their application in higher‐order cycloaddition reaction remains scarce. Herein, we present the [8+3]‐cycloaddition reaction of tropones with in situ generated azaoxyallyl cations allowing the one‐step construction of cycloheptatriene‐fused 1,4‐oxazinones in moderate to good yields. This base‐promoted new carbon‐oxygen and carbon‐nitrogen bond‐forming reaction takes place under mild conditions in the absence of transition metal catalysts.