Chemoselective Sequential Reactions for the Synthesis of 12H-Benzo[a]xanthenes and Dihydro-1H-naphtho[1,2-e][1,3]oxazines

Aziz Shahrisa; Reza Teimuri-Mofrad; Mahdi Gholamhosseini-Nazari

doi:10.1055/s-0034-1380323

Synlett, Table of Contents

Synlett 2015; 26(08): 1031-1038
DOI: 10.1055/s-0034-1380323

letter

Chemoselective Sequential Reactions for the Synthesis of 12H-Benzo[a]xanthenes and Dihydro-1H-naphtho[1,2-e][1,3]oxazines

Authors

Aziz Shahrisa*

Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz 5166614766, Iran Email: ashahrisa@yahoo.com
Reza Teimuri-Mofrad

Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz 5166614766, Iran Email: ashahrisa@yahoo.com
Mahdi Gholamhosseini-Nazari

Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz 5166614766, Iran Email: ashahrisa@yahoo.com

Abstract

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Abstract

Novel sequential Betti–Ullmann and Betti–C–H activation reactions for the synthesis of 12H-benzo[a]xanthenes and dihydro-1H-naphtho[1,2-e][1,3]oxazines have been developed. Depending on the used conditions selective Ullmann-type arylation or α-C-H aryloxylation of 2-bromophenyl alkylaminonaphthols occurred. A simple, fast, green, and high-yielding method for the synthesis of aminonaphthols catalyzed by bismuth(III) chloride under solvent-free conditions is reported.

Key words

chemoselective reactions - sequential reactions - Betti reaction - Ullmann reaction - C–H activation reaction - bismuth (III) chloride - solvent-free reactions

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References

References and Notes

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28 General Procedure for the Synthesis of Aminonaphthols 4a–g To a mixture of 2-naphthol (1 mmol), aldehyde (1 mmol), and amine (1.2 mmol) was added BiCl₃ (7.5 mol%). The mixture was stirred at 80 °C under solvent-free conditions on a preheated oil bath. After completion of the reaction (monitored by TLC, within 12–18 min), the mixture was cooled to r.t., EtOH (10 mL) was added, and the mixture was stirred for 10 min. The obtained solid was collected by filtration and purified by recrystallization from (EtOH–acetone, 4:1) or was subjected to silica gel preparative layer chromatography (EtOAc–n-hexane, 1:5) to give aminonaphthol as a pure solid. Compound 4a: white solid; yield 90%; mp 170–172 °C. FTIR (KBr): ν = 3411, 3053, 2930, 2854, 1561, 1515, 1459, 1248, 1079, 1025 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 1.25–1.77 (6 H, m, CH₂), 2.32–2.45 (2 H, m, NCH), 2.59–2.62 (1 H, m, NCH), 3.30–3.34 (1 H, m, NCH), 5.81 (1 H, s, methine-H), 7.02–7.06 (1 H, m, ArH), 7.13–7.24 (3 H, m, ArH), 7.37 (1 H, t, J = 7.5 Hz, ArH), 7.56–7.61 (2 H, m, ArH), 7.66–7.69 (2 H, m, ArH), 7.83 (1 H, d, J = 8.6 Hz, ArH), 14.38 (1 H, s, OH) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 22.9, 24.9, 25.4, 48.3, 53.8, 68.0, 115.0, 119.1, 120.5, 121.4, 124.6, 125.6, 127.5, 127.6, 127.7, 128.5, 128.6, 130.2, 131.7, 131.8, 137.5, 155.6 ppm. Anal. Calcd for C₂₂H₂₂BrNO: C, 66.67; H, 5.60; N, 3.53. Found: C, 66.48; H, 5.65; N, 3.49.
29 General Procedure for the Synthesis of 12H-benzo[a]xanthene Derivatives 5a–c A mixture of aminonaphthols 4 (0.2 mmol), CuI (10 mol%), picolinic acid (20 mol%), K₃PO₄ (2 equiv) in DMSO (2 mL) was heated at 100 °C for 18 h in a sealed tube. After cooling, the reaction mixture was poured into H₂O and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO₄, and concentrated under reduced pressure. The residue was purified by silica gel preparative layer chromatography (EtOAc–n-hexane, 1:3) to give the desired products 5a–c. Compound 5a: white solid; yield 80%; mp 171–173 °C. FTIR (KBr): ν = 3059, 2928, 2854, 1642, 1516, 1249, 756 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 1.14–1.16 (2 H, m, CH₂), 1.31–1.33 (4 H, m, CH₂), 2.24–2.32 (1 H, m, NCH), 2.32–2.37 (2 H, m, NCH), 2.99 (1 H, m, NCH), 5.39 (1 H, s, methine-H), 7.08–7.12 (1 H, m, ArH), 7.15–7.30 (4 H, m, ArH), 7.34–7.38 (1 H, m, ArH), 7.48–7.52 (1 H, m, ArH), 7.72–7.78 (2 H, m, ArH), 8.12 (1 H, d, J = 8.5 Hz, ArH) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 21.4, 21.6, 23.4, 25.2, 48.4, 56.7, 113.4, 115.1, 116.3, 116.5, 121.6, 122.9, 123.1, 125.5, 127.2, 127.3, 128.3, 128.6, 129.0, 132.9, 152.0, 153.8 ppm. Anal. Calcd for C₂₂H₂₁NO: C, 83.78; H, 6.71; N, 4.44. Found: C, 83.52; H, 6.75; N, 4.40.
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34 General Procedure for the Synthesis of Dihydro-1,3-oxazines Derivatives 6a–f To a solution of aminonaphthols 4 (0.2 mmol) in toluene (3 mL), Cs₂CO₃ (2 equiv), CuI (10 mol%), and l-proline (20 mol%) were added, and the reaction mixture was heated at 110 °C for 6–8 h (monitored by TLC). After cooling, the reaction mixture was poured into H₂O and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO₄, and concentrated under reduced pressure. The residue was purified by silica gel preparative layer chromatography (EtOAc–n-hexane, 1:9) to give the desired products 6a–f. Compound 6a: white solid; yield 74%; mp 165–167 °C. FTIR (KBr): ν = 3060, 2937, 2831, 1620, 1512, 1461, 1242, 1069, 752 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 1.56–1.59 (2 H, m, CH₂), 1.73–1.78 (3 H, m, CH₂), 1.95–1.99 (1 H, m, CH₂), 2.81–2.86 (1 H, m, NCH₂), 3.04–3.06 (1 H, m, NCH₂), 4.95 (1 H, s, NCHO), 5.38 (1 H, s, methine-H), 6.80 (1 H, d, J = 7.5 Hz, ArH), 7.03 (1 H, t, J = 7.5 Hz, ArH), 7.08–7.15 (3 H, m, ArH), 7.25–7.27 (2 H, m, ArH), 7.68–7.76 (3 H, m, ArH). ¹³C NMR (100 MHz, CDCl₃): δ = 17.4, 24.3, 28.3, 46.9, 61.2, 80.2, 109.4, 117.6, 121.6, 122.0, 124.4, 125.6, 125.7, 127.5, 127.7, 128.0, 128.1, 130.3, 131.2, 132.4, 140.6, 151.8. Anal. Calcd for C₂₂H₂₀BrNO: C, 67.01; H, 5.11; N, 3.55. Found: C, 66.78; H, 5.14; N, 3.51.

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