Abstract
A convenient practical approach for the synthesis of 2-(pyridin-2-yl)ethanols by direct benzylic addition of azaarenes and aldehydes under catalyst- and solvent-free conditions is reported. This reaction is metal-free, green, and was carried out in a facile operative environment without using any hazardous transition metal catalysts or any other coupling reagents. Different aromatic aldehydes and azaarenes were monitored, and the yields of the resulting products were moderate to excellent. We accomplished several azaarene derivatives under neat conditions through a highly atom-economical pathway. To evaluate the preparative potential of this process, gram-scale reactions were performed up to a 10 g scale.
Highlights
Azaarenes are a distinct class of heterocyclic compounds possessing wide compatibility in the field of synthetic organic chemistry
Among various nitrogen-containing heterocyclic compounds, pyridine and quinolines are readily found in bioactive compounds [5]
Our investigation started with the reaction of p-nitrobenzaldehyde (2a) and 2,6dimethylpyridine (1a) in the presence of Hβ zeolite as a catalyst at 120 °C in toluene for 24 h in a sealed vial (Table 1, entry 1)
Summary
Azaarenes are a distinct class of heterocyclic compounds possessing wide compatibility in the field of synthetic organic chemistry. To develop advantageous eco-friendly, atom-economical, simple, and efficient synthetic-organic processes under solvent- and catalyst-free conditions in order to synthesize highly demanding pharmaceuticals or natural products can be quite backbreaking [43,44,45]. We disclose environmentally benign, atom-economical, catalyst-free nucleophilic additions of benzylic-like azaarene C–H groups to various benzaldehydes under neat conditions (Scheme 3).
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