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The Mannich reaction in the synthesis of N,S-containing heterocycles 11. Synthesis of 3,3′-(1,4-phenylene)-bis(8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitriles)

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Abstract

N-Methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates readily undergo the Mannich reaction with p-phenylenediamines and excess formaldehyde in the absence of a catalyst to form 3,3′-(1,4-phenylene)-bis(8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitriles) in moderate yields (24–56%).

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Authors and Affiliations

  1. “ChemEx“ Laboratory Vladimir Dal’ East-Ukrainian National University, 20 a kv. Molodezhnyi, 91034, Lugansk, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

  2. Physico-chemical Department, State Enterprise “Luganskstandartmetrology”, 50 ul. Timiryazeva, 91021, Lugansk, Ukraine

    V. V. Dotsenko

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. P. Litvinov

Authors
  1. V. V. Dotsenko
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  2. S. G. Krivokolysko
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  3. V. P. Litvinov
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Correspondence to V. V. Dotsenko.

Additional information

For Part 10, see V. V. Dotsenko, K. A. Frolov, S. G. Krivokolysko, V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2009, 1436 [Russ. Chem. Bull., Int. Ed., 2009, 58, 1479].

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 129–133, January, 2012.

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Dotsenko, V.V., Krivokolysko, S.G. & Litvinov, V.P. The Mannich reaction in the synthesis of N,S-containing heterocycles 11. Synthesis of 3,3′-(1,4-phenylene)-bis(8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitriles). Russ Chem Bull 61, 131–135 (2012). https://doi.org/10.1007/s11172-012-0018-5

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  • DOI: https://doi.org/10.1007/s11172-012-0018-5

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