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Synthesis of polyazaheterocycles containing linearly bound 1,2,4-thiadiazole using enaminones

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Abstract

A reaction of N-substituted 5-amino-3-(2-oxopropyl)-1,2,4-thiadiazoles with dimethylformamide dimethyl acetal gave 3-(5-amino-1,2,4-thiadiazol-3-yl)-4-(dimethylamino)but-3en-2-ones, whose cyclization with hydrazine, guanidine, 1H-pyrazol-5-amines and 6-aminopyrimidin-4(3H)-ones led to 3-methyl-1H-pyrazole, 4-methylpyrimidin-2-amine, 5-methyl3-arylpyrazolo[1,5-a]pyrimidines, and 5-methyl-2-R-pyrido[2,3-d]pyrimidin-4(3H)-ones containing a 5-amino-1,2,4-thiadiazole fragment linearly bound at position 3.

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Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya pl., 394006, Voronezh, Russian Federation

    Kh. S. Shikhaliev, P. S. Romanov, A. S. Shestakov, N. V. Stolpovskaya, M. Yu. Krysin & A. Yu. Potapov

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi pr-d, 142432, Chernogolovka, Moscow Region, Russian Federation

    A. N. Proshin

Authors
  1. Kh. S. Shikhaliev
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  2. P. S. Romanov
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  3. A. S. Shestakov
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  4. N. V. Stolpovskaya
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  5. M. Yu. Krysin
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  6. A. Yu. Potapov
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  7. A. N. Proshin
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Correspondence to Kh. S. Shikhaliev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 1008—1012, April, 2016.

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Shikhaliev, K.S., Romanov, P.S., Shestakov, A.S. et al. Synthesis of polyazaheterocycles containing linearly bound 1,2,4-thiadiazole using enaminones. Russ Chem Bull 65, 1008–1012 (2016). https://doi.org/10.1007/s11172-016-1404-1

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  • DOI: https://doi.org/10.1007/s11172-016-1404-1

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