Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes Via an Unprecedented [2+4] Reaction Topology

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2016 Apr 22

PMID 27097759

Citations 10

Authors

Dmitry M Kuznetsov

Olga A Mukhina

Andrei G Kutateladze

Affiliations

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Abstract

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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