Iodine/Hydrogen Peroxide Promoted Intramolecular Oxidative C–O Bond Formation in Ethanol at Room Temperature: A Green Approach to 1,3-Oxazines

Abstract

An I₂/H₂O₂-promoted intramolecular C–O bond-formation reaction of a variety of 1-(aminoalkyl)-2-naphthols or 2-(aminoalkyl)phenols to give the corresponding 1,3-oxazines was developed. The reaction is simple, atom-economic, and proceeds smoothly at room temperature under metal-free conditions in ethanol as solvent.

Key words

iodine catalysis - aminoalkylnaphthols - aminooalkylphenols - cyclization - oxazines

• References and Notes

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• 24 Oxazines 2a–v; General Procedure I₂ (10 mol%, 25 mg) and 35% aq H₂O₂ (194 mg, 2 equiv) were added to a solution of the appropriate naphthol or phenol 1 (1.0 mmol) in EtOH (3.0 mL), and the mixture was stirred at r.t. for the appropriate time (Figure 2). When the reaction was complete (TLC), the solvent was removed under reduced pressure, and the crude product was purified by column chromatography [silica gel (100–200 mesh), EtOAc–hexane]. 3-Isocyano-12-phenyl-7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine (2m) Brown solid; yield: 196 mg (60%); mp 155–157 °C. IR (KBr): 3081, 2931, 2212, 1622, 1591, 1461, 1344, 1231, 1092 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 8.12 (s, 1 H), 7.76 (d, J = 9.2 Hz, 1 H), 7.44–7.40 (m, 2 H), 7.31–7.24 (m, 3 H), 7.21–7.17 (m, 3 H), 5.43 (s, 1 H), 5.11 (m, 1 H), 3.39–3.35 (m, 1 H), 2.90–2.85 (m, 1 H), 2.16–1.98 (m, 4 H). ¹³C NMR (125 MHz, CDCl₃): δ = 154.5, 142.4, 134.4, 134.2, 129.4, 128.5, 128.4, 127.6, 127.5, 127.2, 123.6, 120.7, 119.6, 110.6, 105.9, 87.1, 56.0, 50.4, 31.8, 20.8. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₂H₁₉N₂O: 327.1497; found: 327.1499. 3-Bromo-12,13-dihydro-7aH,15H-naphtho[1′,2′:5,6][1,3]oxazino[2,3-a]isoquinoline (2r) White solid; yield: 322 mg (88%); mp 188–190 °C. IR (KBr): 3056, 2933, 1620, 1589, 1318, 1241, 1090, 744 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.92 (d, J = 2.0 Hz, 1 H), 7.57–7.52 (m, 3 H), 7.46–7.45 (m, 1 H), 7.36–7.29 (m, 2 H), 7.23–7.22 (m, 1 H), 7.07 (d, J = 8.9 Hz, 1 H), 5.79 (s, 1 H), 4.77 (d, J = 16.6 Hz, 1 H), 4.24 (d, J = 16.6 Hz, 1 H), 3.43–3.38 (m, 1 H), 3.20–3.13 (m, 1 H), 2.96–2.89 (m, 2 H). ¹³C NMR (125 MHz, CDCl₃): δ = 151.9, 134.8, 132.7, 130.6, 130.1, 129.9, 129.7, 129.0, 128.8, 128.4, 127.2, 126.3, 122.9, 119.9, 117.1, 111.3, 86.9, 51.1, 45.1, 29.0. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₀H₁₇BrNO: 366.0494; found: 366.0499 (⁷⁹Br, 100%); 368.0495 (⁸¹Br, 100%). 7a,12,13,15-Tetrahydro-2H-chromeno[8′,7′:5,6][1,3]oxazino-[2,3-a]isoquinolin-2-one (2v) Gummy solid; yield 261 mg (85%). IR (CHCl₃): 3081, 2916, 2841, 1719, 1621, 1548, 1394, 1233, 1146, 743 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.65 (d, J = 9.5 Hz, 1 H), 7.43 (d, J = 6.9 Hz, 1 H), 7.37–7.22 (m, 4 H), 6.76 (d, J = 8.5 Hz, 1 H), 6.26 (d, J = 9.3 Hz, 1 H), 5.90 (s, 1 H), 4.42 (s, 2 H), 3.09–3.03 (m, 4 H). ¹³C NMR (125 MHz, CDCl₃): δ = 161.3, 157.4, 152.1, 144.1, 134.5, 131.7, 129.3, 128.7, 128.4, 126.8, 126.3, 113.8, 112.3, 111.9, 106.8, 88.6, 48.2, 44.3, 28.6. HRMS (ESI): m/z [M + H]⁺ calcd for C₁₉H₁₅NO₃: 306.1130; found: 306.1137.
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