TY - JOUR A1 - Irgashev, Roman A. A1 - Karmatsky, Arseny A. A1 - Rusinov, Gennady L. A1 - Charushin, Valery N. T1 - A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles JF - Beilstein Journal of Organic Chemistry PY - 2015/// VL - 11 SP - 1000 EP - 1007 SN - 1860-5397 DO - 10.3762/bjoc.11.112 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.11.112 KW - aldol-crotonic condensation KW - isatin KW - Lawesson’s reagent KW - methyl ketones KW - Paal–Knorr reaction KW - thieno[2,3-b]indole N2 - A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the “aldol-crotonic” type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene)indolin-2-ones with Lawesson’s reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal–Knorr cyclization, thus affording tricyclic thieno[2,3-b]indoles. ER -