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Mannich reaction in the synthesis of N,S-containing heterocycles. 14*. Unexpected formation of thiazolo[3,2-a]pyridines in the aminoalkylation of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates by isobutyraldehyde and primary amines

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Chemistry of Heterocyclic Compounds Aims and scope

Treatment of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with an excess of isobutyraldehyde and primary aromatic amines in refluxing ethanol gives the corresponding 7-aryl-3-arylamino-2,2-dimethyl-5-oxo-2,3,6,7-tetrahydro-5 H-thiazolo[3,2-a]pyridine-8-carbonitriles in 18-38 % yields.

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Notes

  1. * Overlapping of the signals of the major and minor isomers.

  2. *2 Signals of the minor isomers. Ratio of minor and major isomers in compound 3d ~ 1:4.

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Authors and Affiliations

  1. “ChemEx Laboratory”, Vladimir Dal’ East-Ukrainian National University, 20-A/7 Molodezhny Kv., Lugansk, 91034, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

Authors
  1. V. V. Dotsenko
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  2. S. G. Krivokolysko
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Correspondence to V. V. Dotsenko.

Additional information

*For Communication 13, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 721-725, April, 2012.

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Dotsenko, V.V., Krivokolysko, S.G. Mannich reaction in the synthesis of N,S-containing heterocycles. 14*. Unexpected formation of thiazolo[3,2-a]pyridines in the aminoalkylation of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates by isobutyraldehyde and primary amines. Chem Heterocycl Comp 48, 672–676 (2012). https://doi.org/10.1007/s10593-012-1042-y

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