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Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza‐ o ‐xylylenes via an Unprecedented [2+4] Reaction Topology
Author(s) -
Kuznetsov Dmitry M.,
Mukhina Olga A.,
Kutateladze Andrei G.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602288
Subject(s) - intramolecular force , cycloaddition , synthon , chemistry , combinatorial chemistry , topology (electrical circuits) , photochemistry , computational chemistry , stereochemistry , organic chemistry , catalysis , mathematics , combinatorics
A new method was developed for the photoinduced dearomatization of arenes through an intramolecular cycloaddition with aza‐ o ‐xylylenes generated by excited‐state intramolecular proton transfer (ESIPT) in the readily available photoprecursors. The [2+4] topology of this cycloaddition is unprecedented for photo‐dearomatizations of benzenoid aromatic carbocycles. It provides rapid access to novel heterocycles, cyclohexadieno‐oxazolidino‐quinolinols, as valuable synthons for a broad range of post‐photochemical transformations.