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Synthesis of 3-Amino-6,7-Dihydroferroceno[a]Quinolizin-4-One Derivatives via the Reaction of 3,4-Dihydroferroceno[c]Pyridines with Azlactones

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Chemistry of Heterocyclic Compounds Aims and scope

Derivatives of 3-amino-6,7-dihydroferroceno[a]quinolizin-4-one were obtained by the reaction of 3,4-dihydroferroceno[c]pyridines with 4-(ethoxymethylidene)- and 4-(3-oxo-2-benzofuran-1(3H)-ylidene)-2-phenyl-1,3-oxazol-5(4H)-ones (azlactones) in moderate to good yields. The intermediate products of the addition of 4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5(4H)-one to the alkyl group of 1-alkyl-3,4-dihydroferroceno[c]pyridines were isolated and characterized. The reaction of 4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one with 3,4-dihydroferroceno[c]pyridines led to the formation of derivatives of 3-amino-2-phenyl-3,4,6,7-tetrahydroferroceno[a]quinolizin-4-one, which were oxidized with DDQ to 3-amino-2-phenyl-6,7-dihydroferroceno[a]quinolizin-4-one.

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Notes

  1. Here and further in the experimental part, the signals of both isomers are marked with an asterisk (*).

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Authors and Affiliations

  1. Omsk State Technical University, 11 Mira Ave, Omsk, 644050, Russia

    Vladislav Yu. Shuvalov, Anastasia S. Kostyuchenko & Alexander S. Fisyuk

  2. Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, 3 Akademika Koroleva St, Perm, 614013, Russia

    Yuliya S. Rozhkova, Irina V. Plekhanova & Yurii V. Shklyaev

  3. Dostoevsky Omsk State University, 55a Mira Ave, Omsk, 644077, Russia

    Alexander S. Fisyuk

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  1. Vladislav Yu. Shuvalov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(1), 7–14

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Shuvalov, V.Y., Rozhkova, Y.S., Plekhanova, I.V. et al. Synthesis of 3-Amino-6,7-Dihydroferroceno[a]Quinolizin-4-One Derivatives via the Reaction of 3,4-Dihydroferroceno[c]Pyridines with Azlactones. Chem Heterocycl Comp 58, 7–14 (2022). https://doi.org/10.1007/s10593-022-03050-5

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