A simple and facile synthesis of amidoalkyl naphthols catalyzed by Yb(OTf)₃ in ionic liquids

Abstract

An improved, simple, and facile synthesis of amidoalkyl naphthols by employing three-component one-pot condensation reaction of β-naphthol, aromatic aldehydes, and amides in ionic liquids using ytterbium triflate as a mild Lewis acid catalyst is described. Advantageously, amidoalkyl naphthols were obtained in high yield under eco-friendly, economical, and non-corrosive conditions, and the catalyst was recycled.

Efficient and solvent-free synthesis of 1-amidoalkyl-2-naphthols using N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide

“…Therefore, the following mechanism can be suggested for the synthesis of amidoalkyl naphthols (Scheme 2) [16][17][18][19].…”

“…In recent years, ZrOCl 2 [9] [14], VB 1 [15], P 2 O 5 [16], Yb(OTf) 3 Bmim BF 4 [17], CuPMo [18], NKC-9 [19], and H 3 Mo 12 O 40 P [20] have been utilized, as catalysts, for this synthesis. In continuation of our interest in the application of N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] [21] (Fig.…”

Eco-friendly synthesis of amidochloroalkylnaphthols and its related oxazepinones with biological evaluation

“…Several reports have described the synthesis of amidoalkylnaphthols through multicomponent condensation of aryl aldehydes, 2-naphthol, and carboxylic acid amides in the presence of a Lewis or Bronsted acid catalysis, generally under thermal conditions [31][32][33][34][35][36][37][38][39][40]. Thus, multicomponent condensation of aldehydes, 2-naphthol, and nitriles to give amidoalkylnaphthols in a Ritter-type reaction was also reported [41][42][43][44][45][46][47][48][49].…”

Facile One-Pot Synthesis of 1-Amidoalkyl-2-Naphthols by RuCl2(PPh3)3-Catalyzed Multi-Component Reactions

“…Although numerous methods for the synthesis of 1-amidoalkyl-2-naphthols have been reported, [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] there is still demand for simpler, less toxic, more effective, and milder catalysts. Our interest in developing a mild and efficient synthetic method that provides a variety of 1-amidoalkyl-2-naphthols has led us to looking into more convenient and safely usable catalysts.…”