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Synlett 2013; 24(7): 847-850
DOI: 10.1055/s-0032-1318495
DOI: 10.1055/s-0032-1318495
letter
Facile Synthesis of Pyrido[2,1-a]isoindoles via Iron-Mediated 2-Arylpyridine C–H Bond Cleavage
Weitere Informationen
Publikationsverlauf
Received: 15. Januar 2013
Accepted after revision: 05. März 2013
Publikationsdatum:
15. März 2013 (online)
Abstract
An iron-catalyzed reaction of 2-arylpyridine C–H bond with 2-bromoacetophenone is achieved, providing pyrido[2,1-a]-isoindoles in moderate to good yields. The regioselectivity stems from the domination of hindrance on the regioselective ortho-functionalization of 2-arylpyridines C–H bond.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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- 11 General Experimental Details: Under an air atmosphere, a reaction tube was charged with 2-arylpyridine (0.2 mmol), 2-bromo-1-phenylethanone (0.24 mmol), FeI2 (25 mol%), CsI (0.25 mmol) and toluene–NMP (15:1, 1.5 mL). The mixture was stirred at 130 °C for 48 h in a sealed tube. After the completion of the reaction, as monitored by TLC, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product. (10-Methylpyrido[2,1-a]isoindol-6-yl)(phenyl)-methanone (3d): 1H NMR (500 MHz, CDCl3): δ = 10.70 (d, J = 7.0 Hz, 1 H), 8.37 (d, J = 8.5 Hz, 1 H), 7.67–7.68 (m, 2 H), 7.51–7.55 (m, 4 H), 7.37 (d, J = 7.0 Hz, 1 H), 7.12–7.15 (m, 1 H), 7.00 (d, J = 7.0 Hz, 1 H), 6.71 (d, J = 8.5 Hz, 1 H), 2.88 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 183.8, 142.2, 137.9, 135.1, 132.6, 131.9, 130.5, 128.6, 128.2, 127.7, 125.3, 122.9, 120.2, 118.6, 118.0, 117.0, 114.1, 26.8. IR (prism): 1716, 1578, 1558, 1485, 1473, 1439, 1416, 1297, 1264, 1228, 1165, 1148, 1108, 1043, 1017, 972, 865, 848, 803, 775, 753, 736, 710, 701, 682, 656 cm–1. HRMS (EI): m/z [M + H]+ C20H16NO: 286.1232; found: 286.1225
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