L. Sobenina, D. Tomilin, M. Gotsko
Aug 26, 2014
Citations
0
Influential Citations
21
Citations
Journal
Tetrahedron
Abstract
Abstract (4,5,6,7-Tetrahydroindol-2-yl)alkynes, synthesized by cross-coupling of 4,5,6,7-tetrahydroindoles with aroyl(hetaroyl)bromoalkynes or ethyl bromopropynoate in the presence of K2CO3, regioselectively cyclize with hydroxylamine to either 3- or 5-(4,5,6,7-tetrahydroindol-2-yl)isoxazoles depending on the acidity of the reaction mixture: in the presence of acetic acid 3-isomers are formed (ca. 100% selectivity), while under neutral conditions the reaction is switched to 5-isomers (94–97% selectivity).