One-Pot Two-Step Multicomponent Process of Indole and Other Nitrogenous Heterocycles or Amines toward α‑Oxo-acetamidines

• Published in: Organic letters Vol. 18; no. 8; pp. 1864 - 1867
• Main Authors: Martinez-Ariza, Guillermo, McConnell, Nicholas, Hulme, Christopher
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 15.04.2016; Amer Chemical Soc
• Subjects: Amidines - chemical synthesis; Amidines - chemistry; Amines - chemistry; Carbonates - chemistry; Catalysis; Cesium - chemistry; Chemistry; Chemistry, Organic; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Indoles - chemistry; Molecular Structure; Nitrogen - chemistry; Oxidation-Reduction; Physical Sciences; Science & Technology; UGI-AZIDE; SOLVENT-FREE; ALKYLATION; DRUG DISCOVERY; CATALYST-FREE; PROTEIN-PROTEIN INTERACTIONS; HOT-SPOTS; (3-INDOLYL)GLYCINE DERIVATIVES; FRIEDEL-CRAFTS REACTION; BIFUNCTIONAL BUILDING-BLOCKS
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/acs.orglett.6b00634

A cesium carbonate promoted three-component reaction of N–H containing heterocycles, primary or secondary amines, arylglyoxaldehydes, and anilines is reported. The key step involves a tandem sequence of N-1 addition of a heterocycle or an amine to preformed α-iminoketones, followed by an air- or oxygen-mediated oxidation to form α-oxo-acetamidines. The scope of the reaction is enticingly broad, and this novel methodology is applied toward the synthesis of various polycyclic heterocycles.