Copper-Catalyzed Three-Component One-Pot Synthesis of Substituted 2-Aryl-1,3-benzoselenazoles

Abstract

A simple copper-catalyzed, one-pot synthesis of 2-aryl-1,3-benzoselenazole derivatives was developed using inexpensive, readily available 2-iodoanilines, selenium powder, and aromatic aldehydes as the starting materials. The mild reaction conditions and simple procedure without ligands and other additives make this methodology an alternative for preparing these potential selenium-containing compounds very conveniently.

Key words

multicomponent reactions - heterocycle - 2-aryl-1,3-benzoselenazoles

• References and Notes

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• 32 Typical Procedure for the Synthesis of 2-Aryl-1,3-benzoselenazole 3aaTo a solution of 2-iodoaniline (0.5 mmol) and benzaldehyde (0.6 mmol) in dry DMSO (1.5 mL), selenium powder (1.5 mmol), catalyst (0.05 mmol), and KOH (1.0 mmol) were added, the reaction mixture was stirred in a sealed tube under argon atmosphere at 120 °C for 36 h. After the reaction was finished, the mixture was cooled to r.t., diluted with sat. aq NH₄Cl (15 mL), and extracted with EtOAc (3 × 10 mL). The organic layer was dried over Na₂SO₄, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to afford the corresponding product 3aa. White solid; mp 116.2–117.1 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.12 (d, J = 8.0 Hz, 1 H), 8.06–7.98 (m, 2 H), 7.94 (d, J = 7.8 Hz, 1 H), 7.50–7.46 (m, 4 H), 7.31 (t, J = 7.5 Hz, 1 H). ¹³C NMR (101 MHz, CDCl₃): δ = 172.47, 155.85, 138.33, 136.20, 131.03, 129.06, 128.01, 126.39, 125.26, 124.86, 124.82. HRMS: m/z [M + H]⁺ calcd for C₁₃H₁₀NSe: 259.9973; found: 259.9948.