ChemInform Abstract: Assembly of Substituted 2‐Alkylquinolines by a Sequential Palladium‐Catalyzed C—N and C—C Bond Formation.

Abstract

Assembly of Substituted 2-Alkylquinolines by a Sequential Palladium-Catalyzed C-N and C-C BondFormation. -A range of substituted 2-alkylquinolines is efficiently prepared by reaction of substituted anilines (I) with ethyl vinyl ether (II) or allyl butyl ether (IV) under mild conditions. The synthesis is based on a sequential palladium-catalyzed C-N and C-C bond formation, followed by palladium-catalyzed aromatization, and results in formation of the desired compounds in one step. Resulting products can be further transformed into biologically active compounds for instance, quinoline (X) is the key intermediate for the synthesis of lavendamycin and streptonigrin. Compound (VII) can be applied as a new ligand for phosphorescent iridium complexes which are valuable electroluminescent materials. -(MATSUBARA*, Y.; HIRAKAWA, S.; YAMAGUCHI, Y.; YOSHIDA, Z.-I.; Angew. Chem., Int. Ed. 50 (2011) 33, 7670-7673, http://dx.doi.org/10.1002/anie.201102076 ; Fac. Sci. Eng., Kinki Univ., Higashi-Osaka, Osaka 577, Japan; Eng.) -S. Adam 01-124