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Synthesis of Imidazole Spiro Compounds From 5-Alkoxycarbonyl-1H-Pyrrole-2,3-Diones and Phenylurea

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Chemistry of Heterocyclic Compounds Aims and scope

5-Alkoxycarbonyl-substituted 1H-pyrrole-2,3-diones react with phenylurea, forming alkyl 4-hydroxy-5-oxo-2-[(phenylcarbamoyl)amino]-2,5-dihydro-1H-pyrrole-2-carboxylates, which cyclize in the presence of sodium methoxide, giving 8-hydroxy-3-phenyl-1,3,6-triazaspiro[4.4]-non-8-ene-2,4,7-triones. The crystal structures of 8-hydroxy-9-(4-methylbenzoyl)-3-phenyl-6-(p-tolyl)-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-trione and methyl 8-hydroxy-2,4,7-trioxo-3,6-diphenyl-1,3,6-triazaspiro[4.4]non-8-ene-9-carboxylate were studied.

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This work received financial support from the Ministry of Education and Science of the Russian Federation (project No. 965) and Russian Foundation for Basic Research (project 16-03-590613).

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Authors and Affiliations

  1. Perm State National Research University, 15 Bukireva St., Perm, 614990, Russia

    Aleksei Yu. Dubovtsev, Pavel S. Silaichev, Maksim V. Dmitriev & Andrey N. Maslivets

  2. Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm, 614990, Russia

    Ekaterina S. Denislamova

Authors
  1. Aleksei Yu. Dubovtsev
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  2. Ekaterina S. Denislamova
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  3. Pavel S. Silaichev
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  4. Maksim V. Dmitriev
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  5. Andrey N. Maslivets
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Correspondence to Andrey N. Maslivets.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(7), 467–472

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Dubovtsev, A.Y., Denislamova, E.S., Silaichev, P.S. et al. Synthesis of Imidazole Spiro Compounds From 5-Alkoxycarbonyl-1H-Pyrrole-2,3-Diones and Phenylurea. Chem Heterocycl Comp 52, 467–472 (2016). https://doi.org/10.1007/s10593-016-1913-8

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  • DOI: https://doi.org/10.1007/s10593-016-1913-8

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