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Regio- and stereoselective 1,3-dipolar cycloaddition of indenoquinoxalinone azomethine ylides to β-nitrostyrenes: synthesis of spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizidines] and spiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidines]

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Chemistry of Heterocyclic Compounds Aims and scope

Azomethine ylides obtained in situ from proline or sarcosine and indenoquinoxalinones reacted with nitrostyrenes upon heating in isopropanol for 4–5 days, resulting in the formation of spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizidines] and spiro[indeno[1,2-b]-quinoxaline-11,2'-pyrrolidines] with various regiochemistry.

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Notes

  1. For the purpose of 1Н NMR interpretation, the atom numbering in indeno[1,2-b]pyrido[3,2-e]pyrazine system of compounds 6f–j, 7d,e corresponds to the atom numbering in compounds 6а–е (Scheme 3).

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This work received financial support from the Russian Science Foundation (project 14-13-00388).

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Authors and Affiliations

  1. Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg, 620000, Russia

    Aleksey Yi. Barkov, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev, Igor B. Kutyashev, Vladimir S. Moshkin & Vyacheslav Ya. Sosnovskikh

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  1. Aleksey Yi. Barkov
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  2. Nikolay S. Zimnitskiy
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  3. Vladislav Yu. Korotaev
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  4. Igor B. Kutyashev
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  5. Vladimir S. Moshkin
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  6. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vyacheslav Ya. Sosnovskikh.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(4), 451–459

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Barkov, A.Y., Zimnitskiy, N.S., Korotaev, V.Y. et al. Regio- and stereoselective 1,3-dipolar cycloaddition of indenoquinoxalinone azomethine ylides to β-nitrostyrenes: synthesis of spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizidines] and spiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidines]. Chem Heterocycl Comp 53, 451–459 (2017). https://doi.org/10.1007/s10593-017-2074-0

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