Pirali, TraceyTron, Gian CesareZhu, Jieping2010-11-252010-11-252010-11-25200610.1021/ol061782phttps://infoscience.epfl.ch/handle/20.500.14299/58440By combining three appropriately designed simple substrates, a programmed sequence involving an alpha -isocyano acetamide-based three-component reaction followed by a copper-catalyzed intramol. [3+2] cycloaddn. of alkyne and azide took place to afford complex macrocycles, e.g., I, in moderate to good yields. One macrocycle and two heterocycles were produced with concurrent formation of five chem. bonds in this operationally simple process. [on SciFinder (R)]Cycloaddition reaction ([3+2]; one-pot prepn. of macrocycles via tandem three-component reaction of aldehydesamines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Alcohols Role: RCT (Reactant)RACT (Reactant or reagent) (alkynyl; one-pot prepn. of macrocycles via tandem three-component reaction of aldehydesamines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Amidation; Heterocyclization; Macrocyclization (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydesamines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Aldehydes; Alkynes; Amides; Amines; Azides; Isocyanates Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydesamines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Macrocyclic compounds Role: SPN (Synthetic preparation)PREP (Preparation) (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydesamines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Coupling reaction (three-component; one-pot prepn. of macrocycles via tandem three-component reaction of aldehydesamines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.)azidoamine alkynyl isocyanoacetamide aldehyde tandem coupling intramol cycloaddn copper; macrocycle tricyclo oxazolyl triazolyl deriv prepn; copper tandem coupling intramol cycloaddn catalystOne-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloadditiontext::journal::journal article::research article