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Synlett

Volumn , Issue 11, 2009, Pages 1753-1756

Synthesis of benzoxazoles via intramolecular cyclization of ortho-halobenzanilides using copper fluorapatite catalyst

(5) Lakshmi Kantam, M a Venkanna, G T a Shiva Kumar, K B a Balasubrahmanyam, V a Bhargava, Suresh b

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

b RMIT UNIVERSITY (Australia)

Author keywords

Copper fluorapatite catalyst; Heterogeneous catalyst; Intramolecular cyclization; ortho haloanilides

Indexed keywords

ANILIDE; BENZOXAZOLE DERIVATIVE; COPPER DERIVATIVE; FLUORAPATITE;

ARTICLE; CATALYST; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 67649961478 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217381 Document Type: Article

Times cited : (8)

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- Synthesis of Benzoxazoles; Typical Procedure: Catalyst Cu-FAP (100 mg) was added to a mixture of ortho-haloanilide (1 mmol, and K 2CO3 (2 mmol) in DMF (4 mL) at 110 °C, and the mixture was stirred for 10-20 h. The progress of the reaction was monitored by TLC and on completion of the reaction, the mixture was centrifuged, the centrifugate was treated with ethyl acetate (20 mL) and washed with water. After removing the solvent, the crude material was purified by chromatography on silica gel (60-120 mesh) to afford 2-phenylbenzoxazole (Table 3, Entry 1)11a as a white solid. Mp 101-102 °C; 1H NMR (CDCl3, 300 MHz, δ, 8.25-8.10 (m, 2 H, 7.76-7.70 (m, 1 H, 7.57-7.48 (m, 4 H, 7.33-7.27 (m, 2 H, EI-MS: m/z, 195 [M, 167 (28, 149 (17, 105 (27, 83 (59, 63 (52, 41 42
- +], 167 (28), 149 (17), 105 (27), 83 (59), 63 (52), 41 (42).

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