Hexamethylphosphorous triamide (HMPT)-assisted and Fe2O3nanoparticles (NPs) catalysed approaches towards the formation of C-N bond is described by the reaction between azoles and enone-compounds. The transformations were accomplished under mild conditions at temperatures 25 °C and 50 °C respectively. The efficacy and robustness of the reaction conditions can be envisioned by regioselective construction of N-heterocyclic scaffolds embedded with cycloalkyl residue. The established reaction conditions were found competent over a series of enones and azole derivatives to furnish the desired molecules in high yields ranging from 52-86% under P(III)-mediated conditions and 67-86% under the influences of Fe2O3-NPs as recyclable catalyst.It was observed that the catalyst can be recycled up to six times with good yields of the product.The recognition of cycloalkyl-substituted N-heterocyclic moieties can be realized by their ubiquitous appearances in diversity of bioactive molecules. 1 Importance of these moieties was further witnessed by their occurrences in modern drugs such as phosphoinositide 3-kinase (PI3K) inhibitors, 1a epidermal growth factor receptor (EGFR) inhibitors, 1b cilostazol (to treat peripheral vascular disease), 1c cytochrome P450 (CYP) 17 inhibitors anti-androgens, 1d interleukin-1 receptor-associated kinases (IRAKs) inhibitors 1e (Figure 1). These heterocyclic skeletons were prepared by C-N bond formation approach. In the area of C-N bond formation, the traditionally employed strategy such as aza-Michael protocol holds an important position owing to its advantage over other methodologies. Nevertheless, the preferences of adding azoles to cyclic enones were hindered by the structural complexities of cyclic enones and due to the low nucleophilicity of azoles. 2 According to earlier reported methods, a series of reagents such as metals, 3 bases, 4 organocatalysts, 5 inorganic supports, 6 lanthanides, 7 fluorides, 8 and enzymes 9 have been widely explored to accomplish aza-Michael addition reactions. These transformations were also described under catalyst-free conditions and Brønsted acid-induced conditions, which are operated under harsh conditions at high pressure to deliver unselective product formation. 10,11 Nonetheless, it is noteworthy to mention that the reactions of cyclic enone derivatives with azole molecules using aza-Michael addition approach are rarely explored. 2a,6b,11