Beilstein J. Org. Chem.2018,14, 2907–2915, doi:10.3762/bjoc.14.269
condensation–nucleophilic addition to carbonyl–Michael addition–N-cyclization–elimination–air oxidation sequence to afford structurally intriguing indole–cycloalkyl[b]pyridine-3-carbonitrile hybrid heterocycles in excellent yields.
Keywords: cycloalkyl[b]pyridine-3-carbonitrile; cyclododecanone; 3-(1H-indol-3
-oxopropanenitriles, aromatic aldehydes, cycloalkanones and ammonium acetate. This work also stems from our continuous effort in synthesizing novel cycloalkyl[b]pyridine-3-carbonitrile hybrid heterocycles via tandem/domino reaction [71][72].
Results and Discussion
Initially the precursors viz. 3-(1H-indol-3-yl)-3
–cycloalkyl[b]pyridine-3-carbonitrile hybrid heterocycles have been achieved through a facile one-pot four-component strategy. This reaction occurred through a six-step tandem Hantzsch-like process involving Knoevenagel–Michael–nucleophilic addition–intramolecular cyclization–elimination–oxidative
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Graphical Abstract
Figure 1:
Examples of biologically important cycloalkyl-fused pyridines.