caa a22 4500 445875941 CHVBK 20180317145527.0 cr unu---uuuuu 170323e20111201xx s 000 0 eng 10.1007/s10593-011-0879-9 doi (NATIONALLICENCE)springer-10.1007/s10593-011-0879-9 Khachatryan A. Institute of Organic Chemistry of Scientific-Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Republic of Armenia, 26 Azatutyan Ave., 375014, Yerevan, Republic of Armenia aut Effect of substituents in the propynyl fragment and at the nitrogen atom on the intramolecular cyclization of (3-aryl-2-propynyl)-(4-hydroxy- 2-butynyl)ammonium chlorides and also on the recyclization of the products formed [Elektronische Daten] [A. Khachatryan] Cyclization of dialkyl(4-hydroxy-2-butynyl)[3-(α-naphthyl)-2-propynyl]ammonium chlorides using aqueous KOH solution occurs under more rigorous conditions (1:1 ratio of salt to base) than in the case of their 3-phenyl(p-chlorophenyl, alkenyl)-substituted analogs (5:1 ratio of salt to KOH). Similarly, more rigorous conditions are also needed for the cyclization of (4-hydroxy-2-butynyl)-(3-phenyl-2-propynyl)piperazinium- and dicyclohexylammonium chlorides. In addition to the cyclization products - corresponding dialkyl(7-hydroxymethyl)naphtho[1,2-f]isoindolinium or dialkyl-(4-hydroxy-methyl)benzo[f]isoindolinium chlorides, the products of recyclization of these - dialkyl-amino-phenanthro[1,2-c]furan or dialkylaminonaphtho[1,2-c]furan are also formed. The indicated derivatives become the main products of conversion of the starting salts by a change of salt to KOH ratio, 1:2, and with an increase in the time of the reaction. The results obtained can be explained by steric effect and also the lower thermal stability of the obtained naphtho[1,2-f]isoindolinium salt system compared to the analogous benzo[f]isoindolinium systems. Springer Science+Business Media, Inc., 2011 4-(dialkylaminomethyl)-1,3-dihydrophenanthro[1,2- c ]furans nationallicence 4-(dicyclohexylaminomethyl)-1,3-dihydronaphtho[1,2- c ]furan nationallicence 1-(1,3-dihydronaphtho[1,2-c]furan-4-ylmethyl)-4-( p -fluorophenyl)pipera-zine nationallicence dialkyl(4-hydroxy-2-butynyl)[3-(α-naphthyl)-2-propynyl]ammonium chlorides nationallicence intramolecular cycli-zation and recyclization in the presence of base nationallicence Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/9(2011-12-01), 1091-1097 0009-3122 47:9<1091 2011 47 10593 https://doi.org/10.1007/s10593-011-0879-9 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0879-9 text/html Onlinezugriff via DOI NATIONALLICENCE 100 1- Khachatryan A. Institute of Organic Chemistry of Scientific-Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Republic of Armenia, 26 Azatutyan Ave., 375014, Yerevan, Republic of Armenia aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/9(2011-12-01), 1091-1097 0009-3122 47:9<1091 2011 47 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer