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Synlett 2014; 25(5): 729-735
DOI: 10.1055/s-0033-1340599
DOI: 10.1055/s-0033-1340599
letter
Magnetic Copper Ferrite Nanoparticles: An Inexpensive, Efficient, Recyclable Catalyst for the Synthesis of Substituted Benzoxazoles via Ullmann-Type Coupling under Ligand-Free Conditions
Further Information
Publication History
Received: 01 December 2013
Accepted after revision: 11 December 2013
Publication Date:
15 January 2014 (online)
Abstract
A new sustainable strategy for the synthesis of benzoxazoles from substituted N-(2-halophenyl)benzamides was developed in which inexpensive, readily available, air-stable, recyclable copper(II) ferrite serves as a nanocatalyst. The nanocatalyst can be completely recovered with an external magnet and can be used seven times without significant loss of catalytic activity.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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- 19 2-Phenyl-1,3-benzoxazoles 2; General Procedure A 25 mL Schlenk tube equipped with a magnetic stirring bar was charged with CuFe2O4 nanoparticles (0.05 mmol, 12 mg), benzamide 1 (0.5 mmol), and K2CO3 (1.0 mmol, 139 mg). The tube was evacuated twice and backfilled with N2. DMSO (1.5 mL) was added under N2, the tube was sealed, and then the mixture was stirred at 90–120 °C for 24 h. When the reaction was complete, the solution was cooled to r.t. and concentrated in a rotary evaporator. The residue was purified by column chromatography (silica gel, PE–EtOAc). 2-Phenyl-1,3-benzoxazole (2a) Eluent: PE–EtOAc (20:1); white solid; yield: 94 mg (96%); mp 101–102 °C. 1H NMR (400 MHz, CDCl3): δ = 8.29 (d, J = 7.6 Hz, 2 H), 7.80 (d, J = 3.2 Hz, 1 H), 7.61 (d, J = 3.6 Hz, 1 H), 7.62–7.54 (m, 3 H), 7.38 (d, J = 6.0 Hz, 2 H). 13C NMR (200 MHz, CDCl3): δ = 163.1, 150.8, 142.1, 131.5, 128.9, 127.6, 127.2, 125.1, 124.6, 120.0, 110.6. ESI-MS: m/z = 196.3 [M + H]+. 6-Chloro-2-phenyl-1,3-benzoxazole (2j) Eluent: PE–EtOAc (20:1); white solid; yield: 109 mg (95%); mp 107–108 °C. 1H NMR (400 MHz, CDCl3): δ = 8.26 (d, J = 6.0 Hz, 2 H), 7.71–7.69 (d, J = 8.4 Hz, 1 H), 7.62–7.53 (m, 4 H), 7.36 (d, J = 8.4 Hz, 1 H). 13C NMR (200 MHz, CDCl3): δ = 163.7, 151.0, 141.0, 131.8, 130.7, 129.0, 127.7, 126.7, 125.3, 120.5, 111.3. ESI-MS: m/z = 230.5 [M + H]+.