Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination
作者： Manisha Mishra , Dylan Twardy , Clifford Ellstrom , Kraig A Wheeler , Roman Dembinski
DOI: 10.1039/C8GC02520G
关键词: Aromatization 、 Combinatorial chemistry 、 Ethanol 、 Alkyne 、 Hydroamination 、 Isoquinoline 、 Imine 、 Regioselectivity 、 Catalysis 、 Chemistry
摘要: An efficient environmentally benign route for the synthesis of benzimidazo[2,1-a]isoquinoline has been developed by reacting 2-ethynylbenzaldehyde and related substituted alkynylbenzaldehydes with variously ortho-phenylenediamines aliphatic amines in ethanol. This method provides a convenient, room temperature, atom-economical, catalyst-free access to diversely isoquinoline fused benzimidazoles. Regioselectivity reaction, as referred o-phenylenediamines, was confirmed X-ray crystallography. The reaction found occur three major steps (imine formations, cyclization, aromatization) mechanism proposed.
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