TY - JOUR AU - Izhyk, V.V. AU - Dobrydnev, A.V. AU - Popova, M.V. AU - Volovenko, Yu.M. PY - 2022/12/21 Y2 - 2024/03/29 TI - Synthesis of N-methyl 3-alkyl-isothiazolidine- 1,1-dioxo-3-methylcarboxylates through the intramolecular Michael reaction JF - Reports of the National Academy of Sciences of Ukraine JA - Dopov. Nac. akad. nauk Ukr. VL - IS - 6 SE - Chemistry DO - 10.15407/dopovidi2022.06.073 UR - https://dopovidi-nanu.org.ua/ojs/index.php/dp/article/view/2022-6-9 SP - 73-78 AB - <p>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.</p> ER -