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Study of the reaction of cis- and trans-4-acylamino-3-hydroxythiophans with thionyl chloride

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of cis- and trans-4-acylamino-3-hydroxythiophans with thionyl chloride was studied. It was found that chlorosulfites are initially formed with retention of the configuration of the starting compound. 2-Substituted 3a,4,6,6a-tetrahydrothieno[3,4-d]oxazoline is formed from trans-4-acylamino-3-chlorosulfitothiophans by thermal reaction or in the presence of pyridine, whereas trans-4-acylamino-3-chlorothiophans are obtained from cis-4-acylamino-3-chlorosulfitothiophans; both reactions proceed with inversion of configuration.

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Literature cited

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Authors and Affiliations

  1. All-Union Scientific-Research Vitamin Institute, Moscow

    S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, I. G. Razumova, V. A. Zamureenko & V. M. Berezovskii

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  1. S. D. Mikhno
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  2. T. M. Filippova
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  3. N. S. Kulachkina
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  4. I. G. Razumova
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  5. V. A. Zamureenko
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  6. V. M. Berezovskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 183–187, February, 1975.

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Mikhno, S.D., Filippova, T.M., Kulachkina, N.S. et al. Study of the reaction of cis- and trans-4-acylamino-3-hydroxythiophans with thionyl chloride. Chem Heterocycl Compd 11, 155–158 (1975). https://doi.org/10.1007/BF00471387

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  • DOI: https://doi.org/10.1007/BF00471387

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