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Synthesis of 2-(chloro(methoxy, morpholino)methyl)-hexahydropyrimidothieno[3,2-c]azocines and tetrahydrospiro[pyrido[4,5']thieno[2,3-d]pyrimidines]

Chemistry of Heterocyclic Compounds volume 51, pages 17–25 (2015)Cite this article

2-(Chloromethyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3Н)-ones reacted with acetylenedicarboxylate ester, methyl propiolate or acetylacetylene, forming mixtures of 2-(chloromethyl)-5,6,7,10-tetrahydropyrimido[5',4':4,5]thieno[3,2-d]azocin-4(3Н)-ones and 2'-chloromethyl-6'-methylidene-2,3-dihydro-1Н-spiro[pyrido[4,5']thieno[2,3-d]pyrimidin]-4'(3'H)-ones in various ratios. Analogous products were also obtained in the reaction of 2-(methoxymethyl) derivative with methyl propiolate, while using 2-[(morpholin-4-yl)-methyl] derivative in a similar reaction led to the formation of a more complex product mixture.

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This work received financial support from the Russian Foundation for Basic Research (grant 14-03-00311а).

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Authors and Affiliations

  1. Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Leonid G. Voskressensky, Svetlana A. Kovaleva, Tatiana N. Borisova, Alexander A. Titov, Anna V. Listratova & Alexey V. Varlamov

  2. University of Douala, Faculty of Science, Department of Chemistry, PO Box 2415A, Douala, Republic of Cameroon

    Flavien Toze

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    Viktor N. Khrustalev

Authors
  1. Leonid G. Voskressensky
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  2. Svetlana A. Kovaleva
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  3. Tatiana N. Borisova
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  4. Alexander A. Titov
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  5. Flavien Toze
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  6. Anna V. Listratova
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  7. Viktor N. Khrustalev
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  8. Alexey V. Varlamov
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Corresponding author

Correspondence to Leonid G. Voskressensky.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(1), 17–25

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Voskressensky, L.G., Kovaleva, S.A., Borisova, T.N. et al. Synthesis of 2-(chloro(methoxy, morpholino)methyl)-hexahydropyrimidothieno[3,2-c]azocines and tetrahydrospiro[pyrido[4,5']thieno[2,3-d]pyrimidines]. Chem Heterocycl Comp 51, 17–25 (2015). https://doi.org/10.1007/s10593-015-1652-2

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  • DOI: https://doi.org/10.1007/s10593-015-1652-2

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