Copper catalyzed oxidative cross-coupling of aromatic amines with 2-pyrrolidinone: a facile synthesis of N-aryl-γ-amino-γ-lactams

Copper Catalyzed C−H Activation

“…Various aromatic amines were reacted with 2‐pyrrolidinone with CuO nanoparticles using TBHP as an oxidant and lactams are obtained in good yields with amines having electron withdrawing functional groups. N‐aryl‐γ‐amino‐γ‐lactams were obtained in moderate yields with the homogenous catalysts, CuI, CuCl, CuBr 2 , Cu(OAC) 2 and Cu(SO 4 ) 2 and good yields were obtained with CuO nanoparticles . Sterically hindered amines afforeded lower yields and there is no product formation with benzyl amine, picolyl amine, N,N‐dimethyl amine under the same reaction conditions.…”

“…N-aryl-g-amino-glactams were obtained in moderate yields with the homogenous catalysts, CuI, CuCl, CuBr 2 , Cu(OAC) 2 and Cu(SO 4 ) 2 R D 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 and good yields were obtained with CuO nanoparticles. [51] Sterically hindered amines afforeded lower yields and there is no product formation with benzyl amine, picolyl amine, N,N-dimethyl amine under the same reaction conditions. These results infer that the lactams can be synthesized easily from aromatic and heteroaromatic primary amines.…”

“…Sterically hindered amines afforeded lower yields and there is no product formation with benzyl amine, picolyl amine, N,N‐dimethyl amine under the same reaction conditions. These results infer that the lactams can be synthesized easily from aromatic and heteroaromatic primary amines . The reaction of ethyl 4‐aminobenzoate with 2‐pyrrolidinone was conducted on 10 mmol scale to test the protocol on a higher scale and also the reusability of the catalyst.…”

“…Thecatalyst was reused without any significant loss in activity. The morphology of the used catalyst is same as the fresh catalyst after the reaction . When the reaction was conducted with higher order lactam (δ‐lactam), namely, piperidin‐2‐one with ethyl 4‐aminobenzoate the corresponding δ‐substituted lactam was obtained regioselctively in 68 % yield (Scheme ).…”

A Simple and Facile Synthesis of 4‐Phenylquinoline‐fused Pyrrolidin‐2‐ones

“…Apart from this, pyrrolidin-2-ones, as fundamental building blocks in synthetic chemistry, are used for a wide range of important transformations [10][11][12], which might be another reason for the interest in the synthesis of this class of compounds. On the other hand, as far as the tricyclic 4-phenylquinoline scaffold is concerned, it is also a pharmacologically significant structural unit present in many bioactive compounds, and has been acted as a valuable pharmacophore for drug design [13][14][15].…”