{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,5]],"date-time":"2026-04-05T07:30:07Z","timestamp":1775374207494,"version":"3.50.1"},"reference-count":40,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2022,12,12]],"date-time":"2022-12-12T00:00:00Z","timestamp":1670803200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003443","name":"The Ministry of Education and Science of the Russian Federation","doi-asserted-by":"publisher","award":["075-15-2022-284"],"award-info":[{"award-number":["075-15-2022-284"]}],"id":[{"id":"10.13039\/501100003443","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>N-Arylmaleimides are universal substrates for the synthesis of various heterocyclic compounds with a wide spectrum of biological activity. However, their reactions with thioacetamides have not been comprehensively studied. We studied the reactions of thioacetamide with N-arylmaleimides under various conditions. We established for the first time that three types of products: epithiopyrrolo[3,4-c]pyridines, pyrrolo[3,4-c]pyridines and 3,3\u2032-thiobis(1-arylpyrrolidine-2,5-diones) can be obtained in different conditions. In all cases, two maleimide molecules are involved in the reaction. 3,3\u2032-Thiobis(1-arylpyrrolidine-2,5-diones) are the major products when the reaction is conducted at boiling in acetic acid. When thioacetamide and N-arylmaleimide are kept in dioxane at 50 \u00b0C, epithiopyrrolo[3,4-c]pyridines can be isolated, which, when heated in dioxane, in acetic acid or in methanol in the presence of catalytic amounts of sodium methoxide, are converted into pyrrolo[3,4-c]pyridines by eliminating hydrogen sulfide. The reaction of thioacetamide and N-arylmaleimide in dioxane at boiling temperature with the portioned addition of N-arylmaleimide leads predominantly to the formation of pyrrolo[3,4-c]pyridines. The reaction of thioacetamide with N-alkylmaleimides under all the above conditions leads predominantly to the formation of the corresponding sulfides. The structure of the compounds obtained was characterized by a set of spectral analysis methods and X-ray diffraction (XRD) data.<\/jats:p>","DOI":"10.3390\/molecules27248800","type":"journal-article","created":{"date-parts":[[2022,12,12]],"date-time":"2022-12-12T05:10:19Z","timestamp":1670821819000},"page":"8800","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["New Aspects of the Reaction of Thioacetamide and N-Substituted Maleimides"],"prefix":"10.3390","volume":"27","author":[{"given":"Yulia V.","family":"Aseeva","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Chemistry, Voronezh State University, Universitetskaya Sq. 1, 394018 Voronezh, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nadezhda V.","family":"Stolpovskaya","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Chemistry, Voronezh State University, Universitetskaya Sq. 1, 394018 Voronezh, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8606-458X","authenticated-orcid":false,"given":"Dmitriy Y.","family":"Vandyshev","sequence":"additional","affiliation":[{"name":"Moscow Center of Fundamental and Applied Mathematics, Leninskie Gory Str., 1, 119234 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vladimir B.","family":"Sulimov","sequence":"additional","affiliation":[{"name":"Moscow Center of Fundamental and Applied Mathematics, Leninskie Gory Str., 1, 119234 Moscow, Russia"},{"name":"Research Computing Center, Lomonosov Moscow State University, Leninskie Gory, 1, Building 4, 119234 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mikhail A.","family":"Prezent","sequence":"additional","affiliation":[{"name":"N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4089-3697","authenticated-orcid":false,"given":"Mikhail E.","family":"Minyaev","sequence":"additional","affiliation":[{"name":"N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Khidmet S.","family":"Shikhaliev","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Chemistry, Voronezh State University, Universitetskaya Sq. 1, 394018 Voronezh, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Vandyshev, D.Y., and Shikhaliev, K.S. (2022). 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