Erb, WilliamNeuville, LucZhu, Jieping2010-11-252010-11-252010-11-25200910.1021/jo900210xhttps://infoscience.epfl.ch/handle/20.500.14299/58397Linear amides, prepd. in one step by the Ugi four-component reaction, were converted to 3,4-dihydroquinoxalin-3-ones or to 2-(2-oxoindolin-1-yl)acetamides dependent on the catalytic conditions. While microwave irradn. was found to be determinant on the reaction efficiency, the choice of ligand diverged the reaction pathways. Heating a soln. of the linear amides in dioxane/MeCN (vol./vol. = 85/15) under microwave irradn. conditions in the presence of Pd(dba)2 (0.05 equiv) and Cs2CO3 (2 equiv), using XPhos as a supporting ligand, afforded the 3,4-dihydroquinoxalin-3-ones via an intramol. N-arylation of the secondary amide. On the other hand, using BINAP as ligand under otherwise identical conditions, intramol. alpha -CH arylation of tertiary amide occurred to furnish the oxindoles. [on SciFinder (R)]Amines Role: RCT (Reactant)RACT (Reactant or reagent) (aryl; prepn. of benzopiperazinone derivs. via four-component Ugi addn. of iodoarylamines with carboxylic acidsaldehydes and isocyanides followed by palladium-XPhos-catalyzed heterocyclization under microwave irradn.); Ugi reaction (four-component; prepn. of benzopiperazinone derivs. via four-component Ugi addn. of iodoarylamines with carboxylic acidsaldehydes and isocyanides followed by palladium-XPhos-catalyzed heterocyclization under microwave irradn.); Microwave (irradn.; prepn. of benzopiperazinone derivs. via four-component Ugi addn. of iodoarylamines with carboxylic acidsaldehydes and isocyanides followed by palladium-XPhos-catalyzed heterocyclization under microwave irradn.); Heterocyclization (prepn. of benzopiperazinone derivs. via four-component Ugi addn. of iodoarylamines with carboxylic acidsaldehydes and isocyanides followed by palladium-XPhos-catalyzed heterocyclization under microwave irradn.); Aldehydes; Carboxylic acids; Isocyanides Role: RCT (Reactant)RACT (Reactant or reagent) (prepn. of benzopiperazinone derivs. via four-component Ugi addn. of iodoarylamines with carboxylic acidsaldehydes and isocyanides followed by palladium-XPhos-catalyzed heterocyclization under microwave irradn.)benzopiperazinone deriv prepn; iodophenylaminocarboxamide prepn heterocyclization palladium XPhos; oxindole deriv prepn; palladium BINAP heterocyclization iodophenylaminocarboxamideUgi-post functionalization, from a single set of Ugi-adducts to two distinct heterocycles by microwave-assisted palladium-catalyzed cyclizations: tuning the reaction pathways by ligand switchtext::journal::journal article::research article