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Synthesis of New Heterocyclic Systems on the Basis of 7-Benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthiridine-4-carbonitrile

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Abstract

Methods have been developed for the synthesis of new 8-amino-3-benzyl-5-(morpholin-4-yl)-1,2,3,4-tetrahydropyrimido[4′,5′: 4,5]thieno[2,3-c][2,7]naphthyridine starting from 7-benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile. 8-Hydrazinyl-3-benzyl-5-(morpholin-4-yl)-1,2,3,4-tetrahydropyrimido[4′,5′: 4,5]thieno[2,3-c][2,7]naphthyridine has been converted to isomeric pentacyclic structures with a triazole ring fused through the [c] side of the pyrimidine ring, and their Dimroth rearrangement has been accomplished in both acidic and basic media. New heterocyclic systems containing pyrrolo[1,2-a]pyrimidinone and pyrimido[1,2-a]azepinone fragments were obtained on the basis of the thieno-[2,3-c][2,7]naphthyridine derivative.

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Authors and Affiliations

  1. Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    S. N. Sirakanyan, E. K. Hakobyan & A. A. Hovakimyan

  2. InterBioScreen, Moscow, Russia

    V. G. Kartsev

Authors
  1. S. N. Sirakanyan
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  2. V. G. Kartsev
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  3. E. K. Hakobyan
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  4. A. A. Hovakimyan
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Correspondence to S. N. Sirakanyan.

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Original Russian Text © S.N. Sirakanyan, V.G. Kartsev, E.K. Hakobyan, A.A. Hovakimyan, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 6, pp. 919–923.

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Sirakanyan, S.N., Kartsev, V.G., Hakobyan, E.K. et al. Synthesis of New Heterocyclic Systems on the Basis of 7-Benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthiridine-4-carbonitrile. Russ J Org Chem 54, 923–928 (2018). https://doi.org/10.1134/S1070428018060155

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  • DOI: https://doi.org/10.1134/S1070428018060155

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