Azaanthracenes via Inverse Electron-Demand Diels–Alder Reaction
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Date
2016Author
Kopchuk, Dmitry S.
Chepchugov, N. V.
Taniya, Olga S.
Khasanov, A.F.
Giri,Kousik
Kovalev, Igor S.
Santra, S.
Zyryanov, Grigory V.
Majee, A.
Rusinov, V.L.
Chupakhin, O.N.
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Significance: Azaanthracenes are important fluo- Comment: The benzyne derivative is generated in rophores that are used in a number of applications such as metal or pH sensors. In this report the authors describe a new synthesis of this type of structure via an inverse electron-demand aza- Diels–Alder reaction between a benzyne derivative and an electron-deficient triazine. situ from the diazotization of 2-amino-3-naphthoic acid. It was found that the cyano activating group at the 5-position of the triazine is crucial for the reaction to take place because it offers a smaller energy difference between the cycloaddition HOMO and LUMO.