Synlett 2015; 26(08): 1031-1038
DOI: 10.1055/s-0034-1380323
letter
© Georg Thieme Verlag Stuttgart · New York

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

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
› Author Affiliations
Further Information

Publication History

Received: 07 October 2014

Accepted after revision: 12 February 2015

Publication Date:
12 March 2015 (online)


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.

Supporting Information

 
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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 5ac. 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 6af. 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.