Browsing by Author "Rusinov, V.L."

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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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    A PASE Approach towards (Adamantyl-1)-, Alkyl- and (Het)Aryl-Substituted [1, 2,4]triazolo[1, 5-d][1, 2,4]triazines: A Sequence of Two Solvent-Free Reactions Bearing Lower E-Factors
    (Wiley-Blackwell, 2018) Krinochkin, A.P; Kopchuk, D.S; Giri K.; Shtaitz, Y.K.; Starnovskaya, E.S.; Khalymbadzha, I.A; Drokin, R.A; Ulomsky, E.N.; Santra, S.; Zyryanov, G.V.; Rusinov, V.L.; Chupakhin, O.N.
    A Pot, Atom, Step Economic (PASE) approach is reported towards [1, 2,4]triazolo[1, 5-d][1, 2,4]triazines, substituted with the azole ring with pharmacophore residues, such as 1-adamantyl or 2-furanyl moieties, naproxen residues, as well aliphatic and (het)aromatic substituents, starting from easily available 1,2,4-triazine-5-carbonitriles and carboxylic acids hydrazides. This approach involves a sequence of two solvent-free reactions accompanied by the Dimroth rearrangement on the last step. The structures of the final Dimroth rearrangement products were confirmed based on the DFT studies as well as the single crystal X-ray analysis for the admantane-substituted product. In addition, this method possesses lower E-factors.