Multicomponent reactions of amino alcohols with CH2O and dithiols in the synthesis of 1,3,5-dithiazepanes and macroheterocycles |
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| Institution: | 1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, 450075 Ufa, Russian Federation;2. Ufa Scientific Centre of Russian Academy of Sciences, Institute of Organic Chemistry, 71 Prospekt Oktyabrya, 450054 Ufa, Russian Federation;1. Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan;2. Unit of Elements Strategy Initiative for Catalysts & Batteries, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan;1. Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt;2. Faculty of Education (Khourma), Chemistry Department, Taif University, Saudi Arabia;1. Laboratory of Radiopharmacy, Department of Pharmaceutical Chemistry and Drug Analysis, Faculty of Pharmacy, Medical University of Lodz, 1 Muszynskiego Street, 90-151 Lodz, Poland;2. Central Scientific Laboratory, Medical University of Lodz, 6/8 Mazowiecka Street, 92-215 Lodz, Poland;3. Department of Pharmaceutical Chemistry and Drug Analysis, Faculty of Pharmacy, Medical University of Lodz, 1 Muszynskiego Street, 90-151 Lodz, Poland;1. Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, 8304 Minami-minowa, Kamiina, Nagano 399-4598, Japan;2. Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan |
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| Abstract: | A series of new hydroxyl-substituted 1,3,5-dithiazepanes and N,N′-(2-hydroxyethyl)tetrathiadiazacycloalkanes were synthesized by the multicomponent reactions (MCRs) of amino alcohols with formaldehyde and α,ω-dithiols. The MCR with 1,2-dithiol proceeds via a (1+2+1)-cyclocondensation with selective formation of 1,3,5-dithiazepanes. Stereochemistry of the dithiazepane ring was determined by X-ray diffraction. The reaction with higher α,ω-dithiols (1,3-propane-, 1,4-butane-, 1,5-pentane-, 1,6-hexanedithiol and 2-2-(2-sulfanyletoxy)ethoxy]-1-ethanethiol) yielded OH-substituted macroheterocycles as a result of (2+4+2)-cyclocondensation. The structure of the latter was determined by NMR spectroscopy, MALDI–TOF and electrospray ionization methods. The doubly charged ions like M+2H]2+ are found in the ESI spectra of the macrocycles. |
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| Keywords: | Amino alcohols Cyclization Macrocycles Multicomponent reaction Sulfur heterocycles |
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