FeCl₃-Catalyzed Three-Component One-Pot Synthesis of Novel 4-[(Benzo[d]thiazol-2-ylamino)(phenyl)methyl]-3-hydroxy-9H-xanthen-9-ones

Abstract

A novel three-component one-pot synthesis method using FeCl₃ in DMF as a suitable catalyst and solvent system has been developed for the synthesis of 4-[(benzo[d]thiazol-2-ylamino)(phenyl)methyl]-3-hydroxy-9H-xanthen-9-ones. The method so developed illustrates the successful utilization of 3-hydroxyxanthones in a multicomponent reaction using a variety of aldehydes and 2-aminobenzothiazoles for the first time.

Key words

3-hydroxyxanthone - 2-aminobenzothiazole - multicomponent reaction (MCR) - 2-aminobenzothiazolomethylxanthone - ortho-quinonemethide (OQM)

• References and Notes

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• 29 General Procedure: 3-Hydroxyxanthone (1 mmol), benzaldehyde (1 mmol), and 2-aminobenzothiazole (1 mmol) were added to a 10 mL round-bottom flask. To this DMF (0.3 mL) was added, followed by 0.2 equiv of FeCl₃. The resulting mixture was heated at 120 °C until the reaction was completed as indicated by TLC (ca. 2 h). The reaction mixture is then cooled to r.t., quenched with H₂O, extracted with EtOAc, the combined extracts dried, filtered, the solvent removed, and the residue purified by column chromatography. 4-[(Benzo[d]thiazol-2-ylamino)(phenyl)methyl]-3-hydroxy-9H-xanthen-9-one (4e) Compound 4e was obtained in 91% yield as an off-white solid; mp 180 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 11.73–11.12 (br s, 1 H), 8.85 (d, 1 H, J = 7.8 Hz), 8.11 (dd, 1 H, J ₁ = 7.8 Hz, J ₂ = 1.2 Hz), 8.03 (d, 1 H, J = 8.8 Hz), 7.81 (dt, 1 H, J ₁ = 8.8 Hz, J ₂ = 1.2 Hz), 7.67 (d, 1 H, J = 7.8 Hz), 7.60 (d, 1 H, J = 8.8 Hz), 7.47 (d, 2 H, J = 7.8 Hz), 7.42 (t, 1 H, J = 7.8 Hz), 7.37–7.29 (m, 3 H), 7.22–7.13 (m, 3 H), 7.06 (d, 1 H, J = 8.8 Hz), 7.01 (t, 1 H, J = 6.8 Hz). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 175.4, 166.2, 161.5, 155.8, 152.6, 142.2, 135.1, 131.1, 128.6, 127.3, 127.0, 126.6, 126.0, 125.9, 124.6, 121.5, 121.4, 121.3, 118.8, 118.6, 115.7, 114.8, 114.1, 52.1. IR: ν_max = 3270, 3062, 1639, 1617, 1604, 1573, 1538, 1466, 1439, 1310, 1221, 1148, 1058, 1033, 754, 698 cm^–1. LC–MS: m/z = 449 [M – H]. HRMS: m/z calcd for C₂₇H₁₉O₃N₂S: 451.1111; found: 451.1085.