24 research outputs found

    A Unified Strategy for the Synthesis of β‑Carbolines, γ‑Carbolines, and Other Fused Azaheteroaromatics under Mild, Metal-Free Conditions

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    An efficient, unified approach for the synthesis of β-carbolines, γ-carbolines, and other fused azaheteroaromatics has been realized under metal-free conditions, from propargylic amines and (hetero)­aromatic aldehydes. This unified strategy provides β- and γ-carbolines as well as a range of fused azaheteroaromatics with a broad substrate scope and excellent functional group compatibility. The formal synthesis of oxopropalines D and G has been achieved on gram scale (3a), in a one-pot reaction from commercially available materials (previous shortest reported route to 3a was 5 steps). NMR studies of the conversion of imine intermediate 3aa to β-carboline 3a were conducted and revealed that the reaction proceeded through an allene intermediate

    Rapid Access to 3Substituted Pyridines and Carbolines via a Domino, Copper-free, Palladium-Catalyzed Sonogashira Cross-Coupling/6-Aza Cyclization Sequence

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    Herein, we report a one-pot, three-component method for the preparation of 3-substituted pyridines and carbolines via copper-free, palladium-catalyzed Sonogashira cross-coupling with aryl iodides, followed by 6π-aza cyclization. This arylation cross-coupling/annulation cascade provides easy access to substituted, fused pyridines from readily available substrates in good yields (67–92%) with complete selectivity

    A general method for the metal-free, regioselective, remote C–H halogenation of 8-substituted quinolines

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    An operationally simple, metal-free protocol for regioselective halogenation of a range of 8-substituted quinolines has been established using recyclable trihaloisocyanuric acids.</p
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