Solvent-Regulated Coupling of 2-Alkynylbenzaldehydes with Cyclic Amines: Selective Synthesis of Fused N-Heterocycles and Functionalized Naphthalene Derivatives

He, Yan; Zheng, Zhi; Liu, Qimeng; Zhang, Xinying; Fan, Xuesen

Solvent-Regulated Coupling of 2-Alkynylbenzaldehydes with Cyclic Amines: Selective Synthesis of Fused N-Heterocycles and Functionalized Naphthalene Derivatives

2020

He, Yan | Zheng, Zhi | Liu, Qimeng | Zhang, Xinying | Fan, Xuesen

An efficient synthesis of 1,2,3,4-tetrahydrobenzo[g]quinoline derivatives through PdCl₂-catalyzed, TBHP-promoted, and toluene-mediated dehydrogenation/[4+2] cycloaddition of saturated cyclic amines with 2-alkynylbenzaldehydes was developed. On the contrary, when the reaction medium was changed from toluene to DMSO/H₂O, another class of important compounds, naphthyl chain amines, formed via a dehydrogenation–intermolecular condensation–C–N bond cleavage–intramolecular condensation pathway, was obtained with good selectivity.

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