caa a22 4500 445875666 CHVBK 20180317145527.0 cr unu---uuuuu 170323e20110901xx s 000 0 eng 10.1007/s10593-011-0819-8 doi (NATIONALLICENCE)springer-10.1007/s10593-011-0819-8 Reaction of 5-(2-furyl)-1-methyl-1 H- and 1-methyl-5-(2-thienyl)-1 H -imidazoles with electrophilic reagents [Elektronische Daten] [E. Vlasova, A. Aleksandrov, M. Elchaninov, A. Milov, B. Lukyanov] 5-(2-Furyl)-1-methyl-1H- and 1-methyl-5-(2-thienyl)-1H-imidazoles were synthesized. The electronwithdrawing effect of the 5- and 2-imidazole substituents on the furan ring was studied by 1H NMR spectroscopy and quantum-chemical calculations. Some electrophilic substitution reactions were investigated (nitration, bromination, sulfonation, hydroxymethylation, formylation, and acylation). In some cases, depending on the reaction conditions, both the furan and thiophene ring and the imidazole fragment undergo electrophilic attack. Springer Science+Business Media, Inc., 2011 1-methyl-5-(2-thienyl)-1H-imidazole nationallicence 5-(2-furyl)-1-methyl-1H-imidazole nationallicence quantum-chemical calculations nationallicence directing effect of substituents nationallicence electrophilic substitution nationallicence Vlasova E. South-Russian State Technical University, 132 Prosveshcheniya St., 346428, Novocherkassk, Russia aut Aleksandrov A. South-Russian State Technical University, 132 Prosveshcheniya St., 346428, Novocherkassk, Russia aut Elchaninov M. South-Russian State Technical University, 132 Prosveshcheniya St., 346428, Novocherkassk, Russia aut Milov A. Southern Scientific Center, Russian Academy of Sciences, 41 Chehova St., 344006, Rostov-on-Don, Russia aut Lukyanov B. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., 344090, Rostov-on-Don, Russia aut Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/6(2011-09-01), 684-689 0009-3122 47:6<684 2011 47 10593 https://doi.org/10.1007/s10593-011-0819-8 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0819-8 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Vlasova E. South-Russian State Technical University, 132 Prosveshcheniya St., 346428, Novocherkassk, Russia aut NATIONALLICENCE 700 1- Aleksandrov A. South-Russian State Technical University, 132 Prosveshcheniya St., 346428, Novocherkassk, Russia aut NATIONALLICENCE 700 1- Elchaninov M. South-Russian State Technical University, 132 Prosveshcheniya St., 346428, Novocherkassk, Russia aut NATIONALLICENCE 700 1- Milov A. Southern Scientific Center, Russian Academy of Sciences, 41 Chehova St., 344006, Rostov-on-Don, Russia aut NATIONALLICENCE 700 1- Lukyanov B. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., 344090, Rostov-on-Don, Russia aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/6(2011-09-01), 684-689 0009-3122 47:6<684 2011 47 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer