Nitrogen → 7-(Dimethylamino)-3-ethyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

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Reaction Conditions

Reaction Steps

Pd(PPh3)4 (240 mg, 0.21 mmol) was added to a N2-purged, stirred solution of chloride 112 (550 mg, 1.9 mmol) and SnEt4 (800 mg, 3.4 mmol) in DME (55 mL), and the mixture stirred at 85° C. under N2 for 16 h. The mixture was cooled, the solvent evaporated and the residue purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 115 (250 mg, 47%) as an unstable brown solid: 1H NMR δ 8.23 (s, 1H, H-9), 7.73 (s, 1H, H-5), 3.04-3.33 (m, 5H, H-6, H-7, H-8) 3.02 (q, J=7.6 Hz, 2H, CH2), 2.35 [s, 6H, N(CH3)2], 1.43 (t, J=7.6 Hz, 3H, CH3); 13C NMR δ 167.2, 152.2, 147.6, 146.3, 132.4, 122.9, 114.6, 67.6, 43.8 (2), 38.0, 37.6, 30.6, 12.3; HRMS calcd for C14H18N4O (M+) m/z 258.1481, found 258.1473.

Provenance & Evidence