Multicomponent reaction in deep eutectic solvent for synthesis of substituted 1-aminoalkyl-2-naphthols

Abstract

One-pot multicomponent synthesis of Betti bases (aminoalkyl naphthols) from aldehydes, b-naphthol, and secondary amines in deep eutectic solvent (DES) based on urea and choline chloride has been developed. A broad range of aminoalkyl naphthols can be obtained smoothly in good to excellent yield in biodegradable choline-chloride-based deep eutectic solvent, being compatible with functional groups and operationally straightforward. In addition, DES could be readily recycled at least four times without obvious loss of activity.

Recent advances in the synthesis and synthetic applications of Betti base (aminoalkylnaphthol) and bis-Betti base derivatives

“…Heteroaromatic as well as sterically hindered aromatic aldehydes also gave good product yields with aliphatic aldehydes failing to produce corresponding Betti bases (Scheme 94). 103 Iyer et al 104 achieved a series of 1-((2-hydroxynaphthalen-1yl)(phenyl)(methyl))pyrrolidin-2-one derivatives 138 in 65-90% yields by an efficient iodine (20 mol%)-catalyzed domino reaction involving various aromatic aldehydes, 2-pyrrolidinone and 2-naphthol in CH 2 Cl 2 at room temperature aer 5 h (Scheme 95).…”

Design and identification of nano‐Mg‐[4‐methoxy phenyl‐salicylaldimine–methyl‐pyranopyrzole] Cl2 and its catalytic application on the preparation of 1‐(α‐aminoalkyl)‐2‐naphthols

“…White crystalline solid; M.P. :125–127 °C; lit . M.P:125–126 °C; IR (KBr, cm −1 ): 3452, 3064, 3042, 2969, 2961, 2828, 1621, 1600, 1582, 1513, 1360, 1239, 1119, 942, 877; 1 H NMR (400 MHz, DMSO‐ d 6 ): δ (ppm) 2.46–2.28 (m, 2H), 2.57 (s, 2H), 3.69 (s,7H), 5.43 (d, J = 3.10 Hz, 1H), 6.88 (d, J = 8.30 Hz, 2H), 7.06 (m,1H), 7.27 (d, J = 7.60 Hz, 1H), 7.48–7.35 (m, 1H), 7.54 (d, J = 8.20 Hz, 2H), 7.75 (m,2H), 8.04 (s,1H), 13.26 (s,1H); 13 C NMR (100 MHz, DMSO‐ d 6 ): δ (ppm) 52.4, 55.4, 66.6, 69.8, 114.5, 116.4, 119.9, 122.0, 122.9, 126.9, 128.7, 129.0, 129.6, 130.4, 131.6, 132.4, 154.8, 159.2.…”

“…Hypotensive and bradycardia properties have been reported for 1‐amidoalkyl‐2‐naphthols . One of the important methods for the direct preparation of these considerable compounds is the one‐pot three‐component reaction of aldehyde, 2‐naphthol and amine derivatives …”

“…[12][13][14][15] One of the important methods for the direct preparation of these considerable compounds is the one-pot three-component reaction of aldehyde, 2-naphthol and amine derivatives. [16][17][18][19][20][21][22][23][24] Azomethine compounds, namely Schiff bases are prepared by the reaction of primary amine with carbonyl compounds such as aldehydes or ketones. Schiff base compounds are widely introduced as one of the useful kinds of ligands due to their easy and convenient route for the preparation of materials and their interesting coordination chemistry.…”

Deep Eutectic Solvents as Unconventional Media for Multicomponent Reactions

“…Later, the same authors reported the synthesis of 1-aminoalkyl-2-naphthols (14) from the reaction of β-naphthol, secondary amines and aldehydes using ChCl/urea (1:2) as solvent (Scheme 14). 97…”