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Synthesis of isomeric (E)-[4-(dimethylamino)phenyl]-vinylquinoxalines – precursors for a new class of nonlinear optical chromophores

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Chemistry of Heterocyclic Compounds Aims and scope

Methods are presented for the preparation of isomeric (Е)-3-, (Е)-6-, (Е)-7-[4-(dimethylamino)phenylethenyl]quinoxalin-2-ones and 2-phenylquinoxalines – compounds of “donor–π-bridge” type, which serve as precursors for new nonlinear optical chromophores with potentially high first hyperpolarizability values. The introduction of dimethylanilinoethenyl moiety at position 3 of the quinoxaline system was achieved in good yields by fusion of 3-methyl derivatives with 4-(dimethylamino)benzaldehyde at 220°С in the presence of catalytic amounts of acetic anhydride and pyridine during the synthesis of 3-(dimethylaminophenylethenyl)quinoxalin-2-ones or as a result of condensation of these reactants by the action of 20 М sodium hydroxide solution in the presence of Aliquat 336 during the synthesis of 3-(dimethylaminophenylethenyl)-2-phenylquinoxalines. The introduction of dimethylanilinoethenyl moiety at positions 6 and 7 was achieved by Heck reaction of p-dimethylaminovinylbenzene with 6- or 7-bromoquinoxalines in the presence of palladium acetate. The structures of isomeric 6-bromo- and 7-bromo-3-methyl derivatives of quinoxalines were confirmed by X-ray diffraction analysis.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan, 420088, Russia

    Sirina M. Sharipova, Alina A. Gilmutdinova, Dmitry B. Krivolapov, Olga N. Kataeva & Alexey A. Kalinin

  2. A. M. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya St., Kazan, 420008, Russia

    Zilya R. Khisametdinova

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  1. Sirina M. Sharipova
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  2. Alina A. Gilmutdinova
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  3. Dmitry B. Krivolapov
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  4. Zilya R. Khisametdinova
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  5. Olga N. Kataeva
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  6. Alexey A. Kalinin
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Correspondence to Alexey A. Kalinin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 504–510

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Sharipova, S.M., Gilmutdinova, A.A., Krivolapov, D.B. et al. Synthesis of isomeric (E)-[4-(dimethylamino)phenyl]-vinylquinoxalines – precursors for a new class of nonlinear optical chromophores. Chem Heterocycl Comp 53, 504–510 (2017). https://doi.org/10.1007/s10593-017-2084-y

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