Oxazolidin-2-one-Promoted CuI-Catalyzed Amidation of Aryl Halides and Cyclization of o-Halobenzanilides

Abstract

Oxazolidin-2-one was found to be a versatile and efficient ligand for the CuI-catalyzed amidation of aryl halides and the cyclization of ortho-halobenzanilides. Notably, the less active halides could also be applied successfully in the synthesis of benzoxazoles and benzothiazoles.

Key words

amidation - cyclizations - catalysis - ligand - coupling

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21

General Procedure for the Coupling of Halides with Amides: To a solution of MeONa (2.3 mmol) in DMSO (2 mL) were added CuI (29 mg, 0.15 mmol) and L¹ (26 mg, 0.3 mmol). After stirring the mixture at r.t. for 30 min, the halide (1.5 mmol) and the amide (1.5 mmol) were added to the flask, and the reaction mixture was stirred at 120 °C for
24 h. The mixture was cooled to r.t., H₂O (10 mL) was added, and the resulting suspension was extracted with EtOAc (4 × 10 mL). The extracted layer was dried over MgSO₄, then concentrated, and purified by column chromatography on silica gel to provide the desired products.

22

3-(Pyridin-2-yl)quinazolin-4(3 H )-one (3q): bright yellow solid; mp 135-137 °C(uncorrected). IR (KBr): 3448, 2924, 1688, 1610, 1590, 1563, 1478, 1440, 1294, 1255, 774, 760 cm^-1. ¹H NMR (400 MHz, CDCl₃): δ = 8.65-8.66 (d, J = 4.4 Hz, 1 H), 8.57 (s, 1 H), 8.22-8.24 (d, J = 8.0 Hz, 1 H), 8.06-8.08 (t, J = 7.2 Hz, 1 H), 7.83-7.91 (m, 2 H), 7.74-7.76 (d,
J = 8.0 Hz, 1 H), 7.54-7.63 (m, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 160.1, 149.9, 149.6, 147.8, 146.1, 138.9, 135.4, 128.0, 127.8, 126.9, 124.6, 122.6, 122.1. LRMS (EI, 20 eV): m/z (%) = 223 (100) [M⁺]. Anal. Calcd for C₁₃H₉N₃O: C, 69.95; H, 4.06; N, 18.82. Found: C, 69.46; H, 4.38; N, 18.65.