Journal of the Chemical Society Perkin Transactions 1 · 1988 · 63 citations · 0 references
Cross-coupling ReactionDerivative (Chemistry)EngineeringHeterocyclicLarge ScaleAmides R1conh2N-substituted Amides R1conhch2rOrganic ChemistryChemistryHeterocycle ChemistryNovel Two-step ProcedureSynthetic ChemistryBiomolecular Engineering
Benzotriazole, aldehydes RCHO, and amides R1CONH2 react together with elimination of water to form 1:1:1 adducts which are reduced smoothly by NaBH4 to give the N-substituted amides R1CONHCH2R. Both steps occur in high yields and can be carried out on a large scale, thus comprising a convenient general method for the N-alkylation of amides.