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Investigation of the reactivities and tautomerism of azolidines. 42. 2-Iminothiazolidin-4-ones in the mannich reaction with secondary amines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The aminomethylation of 2-iminothiazolidin-4-one with aqueous formaldehyde and piperidine gives 2-piperidinomethylamino-5-hydroxymethyl-5-piperidinomethylthiazolin-4-one, as well as a compound with an unestablished structure, rather than 3-piperidinomethyl-2-iminothiazolidin-4-one, as was previously assumed. The aminomethylation of 2-iminothiazolidin-4-one with diphenylamine and diethylamine leads to the formation of 2-monoaminomethyl derivatives. 2-Imino-5-benzylidenethiazolidin-4-one reacts with paraformaldehyde and piperidine in benzene to give 2-piperidinomethylimino-3-[(3-piperidinomethyl-4-oxo-5-benzylidenethiazolidin-2-ylidene)iminomethyl]-5-benzylidenethiazolidin-4-one.

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Literature cited

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Authors and Affiliations

  1. Lensovet Leningrad Technological Institute, 198013, Leningrad

    S. Yu. Solov'eva, S. M. Ramsh & A. I. Ginak

Authors
  1. S. Yu. Solov'eva
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  2. S. M. Ramsh
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  3. A. I. Ginak
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Additional information

See [1] for communication 41.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1352–1356, October, 1983.

The authors thank A. V. Dogadin for recording and discussing the PMR spectra.

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Solov'eva, S.Y., Ramsh, S.M. & Ginak, A.I. Investigation of the reactivities and tautomerism of azolidines. 42. 2-Iminothiazolidin-4-ones in the mannich reaction with secondary amines. Chem Heterocycl Compd 19, 1076–1080 (1983). https://doi.org/10.1007/BF00505756

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  • DOI: https://doi.org/10.1007/BF00505756

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