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

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journal contribution
posted on 01.10.2018, 18:40 by Dilipkumar Uredi, Damoder Reddy Motati, E. Blake Watkins
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.