Abstract:
3-Diethoxymethyl-3-hydroxy-3,9-dihydro-2H-benz[4,5]imidazo[2,1-b]thiazol-4-ium salts were synthesized by reaction of chloro oxiranes or isomeric α-chloro ketones with 2-mercaptobenzimidazole. The acetal group of the aforementioned salts undergoes hydrolysis in acidic medium to liberate aldehyde which would react with the NH-moiety of mercaptobenzimidazole, thus leading to cycle expansion with the formation of 3,3,4-trihydroxy-3,4-dihydro-2H-benz[4,5]imidazo[2,1-b][1,3]thiazinium salts. In DMSO solution, the 3,3,4-trihydroxythiazine moiety of the latter compounds is oxidized into 3,4-dioxothiazine one existing in enol form.
Citation:
F. I. Guseinov, M. F. Pistsov, V. M. Malinnikov, O. M. Lavrova, E. M. Movsumzade, L. M. Kustov, “Recyclization of diethoxymethyl substituted benzimidazo-fused thiazolium salts”, Mendeleev Commun., 30:5 (2020), 674–675
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https://www.mathnet.ru/eng/mendc1290
https://www.mathnet.ru/eng/mendc/v30/i5/p674
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Atash V. Gurbanov, Firudin I. Guseinov, Aida I. Samigullina, Tuncer Hökelek, Khudayar I. Hasanov, Tahir A. Javadzade, Alebel N. Belay, “Syntheses, crystal structures, Hirshfeld surface analyses and crystal voids of 1-(4-bromophenyl)-2,2-dichloroethan-1-one and 2,2-dibromo-1-(p-tolyl)ethan-1-one”, Acta Crystallogr E Cryst Commun, 81:2 (2025), 120
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Lesya M. Saliyeva, Nataliia Yu. Slyvka, Mykola I. Korotkykh, Mykhailo V. Vovk, “Methods for the synthesis of imidazo[2,1-b][1,3]thiazines, their annulated and hydrogenated analogs”, Chem Heterocycl Comp, 59:6-7 (2023), 368
Firudin I. Guseinov, Aleksandr V. Knyazev, Elena V. Shuvalova, Konstantin I. Kobrakov, Aida I. Samigullina, Zeliha Atioğlu, Mehmet Akkurt, Ajaya Bhattarai, “Synthesis, crystal structure and Hirshfeld surface analysis of (2Z,2′E)-2,2′-(3-methoxy-3-phenylpropane-1,2-diylidene)bis(hydrazine-1-carbothioamide) dimethylformamide monosolvate”, Acta Crystallogr E Cryst Commun, 79:10 (2023), 910
Firudin I. Guseinov, Vladislav M. Malinnikov, Kirill N. Lialin, Konstantin I. Kobrakov, Elena V. Shuvalova, Yulia V. Nelyubina, Bogdan I. Ugrak, Leonid M. Kustov, Kamran T. Mahmudov, “Charge-assisted chalcogen bonding in 2-(4-substituted benzoyl)thiazolo[3,2-a]pyridin-4-ium bromides”, Dyes and Pigments, 197 (2022), 109898
A. A. Kolodina, D. V. Steglenko, E. S. Khodykina, N. I. Gaponenko, M. S. Galkina, O. P. Demidov, A. V. Metelitsa, “Unusual cyclization of N-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization”, Mendeleev Commun., 32:3 (2022), 386–389
Lin Jiang, Peiying Peng, Liudong Yu, Dengbang Jiang, Yidan Wang, Hongli Li, Minglong Yuan, Mingwei Yuan, “Regio- and diastereoselective synthesis of 3,4-dihydro-2H-benzo [4,5]imidazo[2,1-b] [1,3]thiazine derivatives via DBU-catalyzed [3+3] annulation of MBH carbonates with 2-mercaptobenzimidazoles”, Tetrahedron, 98 (2021), 132430
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