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Synthesis of pyrimidinethiones and spiropyrans proceeding from Mannich ketones

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Abstract

New synthetic opportunities of conjugated and saturated β-aminoketones were revealed consisting in heterocyclization reactions with the formation of spirochromenes and hydropyrimidinethiones. Alicyclic conjugated Mannich bases under conditions of basic catalysis suffer deamination followed by [4+2]-cycloaddition leading to the stereo- and regiodirected formation of difficultly available spirochromene derivatives. Three-component condensation of acyclic and alicyclic Mannich ketones with thiourea and aromatic aldehydes under aprotic acid catalysis afforded functionalized derivatives of pyrimidine-2-thione series. Optimum conditions were found for О,N-heterocyclization of β-aminocarbonyl substrates.

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Authors and Affiliations

  1. Chernyshevskii Saratov State University, Astrakhanshaya ul. 83, Saratov, 410012, Russia

    M. P. Shchekina, R. S. Tumskii, I. N. Klochkova & A. A. Anis’kov

Authors
  1. M. P. Shchekina
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  2. R. S. Tumskii
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  3. I. N. Klochkova
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  4. A. A. Anis’kov
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Correspondence to A. A. Anis’kov.

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Original Russian Text © M.P. Shchekina, R.S. Tumskii, I.N. Klochkova, A.A. Anis’kov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 265–270.

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Shchekina, M.P., Tumskii, R.S., Klochkova, I.N. et al. Synthesis of pyrimidinethiones and spiropyrans proceeding from Mannich ketones. Russ J Org Chem 53, 263–269 (2017). https://doi.org/10.1134/S107042801702021X

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  • DOI: https://doi.org/10.1134/S107042801702021X

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