Brønsted Acid Ionic-Liquid-Catalyzed Facile One-Pot Synthesis of 1-[(1,3-Benzothiazol-2-ylamino)methyl]-2-naphthols in a Green Medium

Abstract

A rapid, simple, and efficient one-pot protocol has been developed for the sustainable synthesis of 1-[(1,3-benzothiazol-2-ylamino)methyl]-2-naphthols from substituted 2-aminobenzothiazoles, aryl aldehydes, and 2-naphthol by using 5 mol% of a Bronsted acid ionic liquid as a catalyst. This method offers several advantages such as a broad substrate scope, short reaction time, one-pot procedure, benign medium, and a high yield using a low catalyst loading. Moreover, the ionic liquid catalyst can be recycled up to three times without a noteworthy loss in catalytic activity.

Key words

aminobenzothiazoles - naphthols - ionic liquid catalysis - organocatalysis

• References and Notes

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• 35 1-[(1,3-Benzothiazol-2-ylamino)(phenyl)methyl]-2-naphthol (7a); Typical Procedure A dried 25-mL round-bottomed flask was successively charged with 2-aminobenzothiazole (4a; 1 equiv), benzaldehyde (5a; 1 equiv), 2-naphthol (6; 1 equiv), and [BCMIM][Cl] (3) in EtOH (5 mL). The mixture was then heated at 80 °C for 15 min (5 mol%) until the reaction was complete (TLC). The solid precipitate was collected by filtration, washed with Et₂O and hexane, and vacuum dried to give a white solid; yield: 95%; mp 200–201 °C. FTIR (ATR): 3388, 1627, 1590, 1530, 1438, 1330, 1272, 1200, 1046, 1027, 942, 837, 814, 748, 696, 612, 557, 494, 424 cm^–1. ¹H NMR (400 MHz, DMSO-d ₆): δ = 10.15 (s, 1 H), 8.80 (d, J = 7.2 Hz, 1 H), 7.81 (dd, J = 19.7, 12.3 Hz, 3 H), 7.67 (d, J = 7.6 Hz, 1 H), 7.34 (dd, J = 17.1, 7.4 Hz, 3 H), 7.30–7.13 (m, 8 H), 7.01 (t, J = 7.6 Hz, 1 H). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 166.77, 153.62, 152.54, 142.94, 132.57, 131.21, 130.05, 129.03, 128.59, 126.67, 126.49, 125.93, 122.90, 122.90, 121.49, 121.37, 119.12, 118.81, 118.56, 53.51.