caa a22 4500 445876743 CHVBK 20180317145530.0 cr unu---uuuuu 170323e20111101xx s 000 0 eng 10.1007/s10593-011-0860-7 doi (NATIONALLICENCE)springer-10.1007/s10593-011-0860-7 Synthesis and tautomerism of 2-phenacyl-1 H -benzimidazoles and their hydrogen bromide salts [Elektronische Daten] [I. Dzvinchuk, A. Nesterenko, V. Polovinko, A. Ryabitskii, M. Lozinskii] 2-Phenacyl-1H-benzimidazoles were prepared by the acylation of 2-methylbenzimidazole using aroyl chlorides with subsequent alcoholysis or aminolysis of the N,C,O-triacylation products obtained. Treatment of the 2-phenacyl-1H-benzimidazoles with hydrobromic acid gave the corresponding salts. The structure of the products was supported by IR, 1H and 13 C NMR, and HMBC spectroscopy as well as by quantum-chemical calculations. 2-Phenacyl-1H-benzimidazoles in DMSO-d6 solution were found to display predominantly imino-enamino tautomerism, while their salts were found to display predominantly keto-enol tautomerism. Springer Science+Business Media, Inc., 2011 benzimidazoles nationallicence acylation nationallicence deacylation nationallicence quantum-chemical study nationallicence spectroscopy nationallicence tautomerism nationallicence Dzvinchuk I. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., 02094, Kyiv, Ukraine aut Nesterenko A. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., 02094, Kyiv, Ukraine aut Polovinko V. Ukrorgsintez, 29 Shchorsa St., 02042, Kyiv, Ukraine aut Ryabitskii A. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., 02094, Kyiv, Ukraine aut Lozinskii M. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., 02094, Kyiv, Ukraine aut Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/8(2011-11-01), 953-963 0009-3122 47:8<953 2011 47 10593 https://doi.org/10.1007/s10593-011-0860-7 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0860-7 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Dzvinchuk I. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., 02094, Kyiv, Ukraine aut NATIONALLICENCE 700 1- Nesterenko A. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., 02094, Kyiv, Ukraine aut NATIONALLICENCE 700 1- Polovinko V. Ukrorgsintez, 29 Shchorsa St., 02042, Kyiv, Ukraine aut NATIONALLICENCE 700 1- Ryabitskii A. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., 02094, Kyiv, Ukraine aut NATIONALLICENCE 700 1- Lozinskii M. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., 02094, Kyiv, Ukraine aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/8(2011-11-01), 953-963 0009-3122 47:8<953 2011 47 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer