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Functionalization of 4-(Diethoxyphosphoryl)-4,7-dihydro5H-thiopyrano[3,4-b]furan-5-carboxylic Acid Ester at the α-Position of the Furan Fragment

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Abstract

On an example of aminomethylation, chloromethylation, and acetylation reactions, it was shown that ethyl 4-(diethoxyphosphoryl)-4,7-dihydro-5H-thiopyrano[3,4-b]furan-5-carboxylate selectively enters the electrophilic substitution reactions at the position 2. The interaction of the obtained 2-chloromethyl derivative with O-, S- and N-nucleophiles was studied. Based on the 2-acetyl derivative, a 4-substituted 1,2,3-thiadiazole ring was formed under the conditions of the Hurd–Mori reaction.

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ACKNOWLEDGMENTS

The studies were carried out using the equipment of the resource center of St. Petersburg State University “Methods of analysis of the composition of matter.”

Funding

The work was carried out within the framework of the state task of the Ministry of Science and Higher Education of Russia no. 785.00X6019 using the equipment of the engineering center of the St. Petersburg State Institute of Technology (Technical University).

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), 190013, St. Petersburg, Russia

    L. M. Pevzner, A. A. Ostrovskaya, M. L. Petrov & A. V. Stepakov

  2. Saint Petersburg State University, 198504, St. Petersburg, Russia

    A. V. Stepakov

Authors
  1. L. M. Pevzner
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  2. A. A. Ostrovskaya
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  3. M. L. Petrov
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  4. A. V. Stepakov
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Correspondence to L. M. Pevzner.

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Pevzner, L.M., Ostrovskaya, A.A., Petrov, M.L. et al. Functionalization of 4-(Diethoxyphosphoryl)-4,7-dihydro5H-thiopyrano[3,4-b]furan-5-carboxylic Acid Ester at the α-Position of the Furan Fragment. Russ J Gen Chem 92, 1919–1929 (2022). https://doi.org/10.1134/S1070363222100073

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  • DOI: https://doi.org/10.1134/S1070363222100073

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