Synthesis of N-methyl 3-alkyl-isothiazolidine- 1,1-dioxo-3-methylcarboxylates through the intramolecular Michael reaction

Authors

DOI:

https://doi.org/10.15407/dopovidi2022.06.073

Keywords:

sulfonamides, amino acids, cyclization, the Michael addition

Abstract

An efficient and common method for the synthesis of N-methyl 3-alkyl-isothiazolidine-1,1-dioxo-3-methylcarboxylates has been developed. Readily available 2-monosubstituted β-amino acid esters hydrochlorides and β-chloroethylsulfonyl chloride were used as starting reagents. Methyl 2-alkyl-2-(vinylsulfonamido)ethanoates obtained on the first step were alkylated at the Nitrogen atom and converted into methyl 2-alkyl-2-(N-methylvinylsulfonamido) ethanoates. The latter were subjected to NaH-mediated intramolecular Michael addition thus affording the target methyl 3-alkyl-isothiazolidine-1,1-dioxo-3-methylcarboxylates. This class of compounds is considered as sulfonamide bioisostere of natural pyroglutamic acid (pGlu) and thus can be used in the synthesis of compounds with potential biological activity.

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Published

21.12.2022

How to Cite

Izhyk В. ., Dobrydnev О. ., Popova М. ., & Volovenko Ю. . (2022). Synthesis of N-methyl 3-alkyl-isothiazolidine- 1,1-dioxo-3-methylcarboxylates through the intramolecular Michael reaction. Reports of the National Academy of Sciences of Ukraine, (6), 73–78. https://doi.org/10.15407/dopovidi2022.06.073