Browsing by Author "Khasanov, A.F."

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    Azaanthracenes via Inverse Electron-Demand Diels–Alder Reaction
    (THIEME STUTTGART, 2016) 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.
    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.
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    Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels-Alder reaction versus aryne-mediated domino process
    (Royal Society of Chemistry, 2018) Kopchuk, D.S.; Nikonov, I.L.; Khasanov, A.F.; Giri, Koushiki.; Santra, S.; Kovalev, I.S.; Nosova, E.V.; Gundala, S.; Venkatapuram, P.; Zyryanov, G.V.; Majee, A.; Chupakhin, O.N.
    The interactions between substituted 5-R-3-(pyridyl-2)-1,2,4-triazines with in situ generated substituted aryne intermediates have been studied. The reaction afforded either inverse demand (ID) aza-Diels-Alder products or 1,2,4-triazine ring rearrangement (domino) products as major ones depending on the nature of both the substituents at the C5 position of the 1,2,4-triazine core or in the aryne moiety. The structures of the key products were confirmed based on X-ray data. Based on the density functional theoretical (DFT) studies of the Diels-Alder transition state geometries, the influence of the nature of arynes on the direction of the 1,2,4-triazine transformation has been proposed.