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One-Pot Syntheses with 2-Substituted 6-Aminopyrimidin-4(3H)-ones: New 5-Aryl-5,8,9,10-tetrahydropyrimido[4,5-b]-quinoline-4,6(3H,7H)-diones and 5,5′-(Arylmethylene)-bis[6-amino-2-methylpyrimidin-4(3H)-ones]

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Abstract

One-pot condensation of 2-substituted 6-aminopyrimidin-4(3H)-ones with aromatic aldehydes and 5,5-dimethylcyclohexane-1,3-dione (dimedone) in acetic acid without a catalyst afforded new substituted 5-aryl-5,8,9,10-tetrahydropyrimido[4,5-b]quinoline-4,6(3H,7H)-diones in good yields. The condensation of 2-memyl-6-aminopyrirnidin-4(3H)-one with aromatic aldehydes at a molar ratio of 2:1 under similar conditions led to the exclusive formation of uncyclized 5,5′-(arylmemylene)bis[6-amino-2-methylpyrimidin-4(3H)-ones].

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Authors and Affiliations

  1. Russian-Armenian (Slavic) University, Yerevan, 0051, Armenia

    A. A. Harutyunyan

  2. Mnjoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, Yerevan, 0014, Armenia

    A. A. Harutyunyan, S. G. Israyelyan, H. A. Panosyan, M. R. Hakobyan & T. R. Hovsepyan

Authors
  1. A. A. Harutyunyan
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  2. S. G. Israyelyan
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  3. H. A. Panosyan
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  4. M. R. Hakobyan
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  5. T. R. Hovsepyan
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Correspondence to A. A. Harutyunyan or T. R. Hovsepyan.

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The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1909–1915.

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Harutyunyan, A.A., Israyelyan, S.G., Panosyan, H.A. et al. One-Pot Syntheses with 2-Substituted 6-Aminopyrimidin-4(3H)-ones: New 5-Aryl-5,8,9,10-tetrahydropyrimido[4,5-b]-quinoline-4,6(3H,7H)-diones and 5,5′-(Arylmethylene)-bis[6-amino-2-methylpyrimidin-4(3H)-ones]. Russ J Org Chem 55, 1896–1901 (2019). https://doi.org/10.1134/S1070428019120145

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  • DOI: https://doi.org/10.1134/S1070428019120145

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