Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza‐ o ‐xylylenes via an Unprecedented [2+4] Reaction Topology | Zendy

Kuznetsov Dmitry M. | Zendy; Mukhina Olga A. | Zendy; Kutateladze Andrei G. | Zendy

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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.

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