Synthesis of Annulated Arenes and Heteroarenes by Hydriodic Acid and Red Phosphorus Mediated Reductive Cyclization of 2-(Hetero)aroylbenzoic Acids or 3-(Hetero)arylphthalides

Abstract

Annulated arenes and hetarenes were prepared in good to very good yields by hydriodic acid/red phosphorus mediated reductive cyclization of 3-(hetero)aryl phthalides. The reductive cyclization also proceeded successfully with 2-aroylbenzoic acids and 2-aroylnaphthoic acids.

Key words

polycycles - anthracenes - tetracenes - hydriodic acid - red phosphorus - reductive cyclization

• References and Notes

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• 28 Reductive Cyclization of Keto Acid 6: Typical Procedure 57% aq HI (2.49 mL, 20 mmol) and red phosphorus (0.37 g, 12 mmol) were added to a solution of keto acid 6 (0.4 g, 1.0 mmol) in glacial AcOH (30 mL), and the mixture was refluxed for 24 h. The red phosphorus was then removed by filtration. The filtrate was mixed with ice–water (100 mL), and the precipitated solid was collected by filtration, washed successively with 10% aq Na₂S₂O₃ (30 mL) and H₂O (60 mL), and air-dried. The crude product was purified by column chromatography (silica gel, hexane) to afford 5-hexylnaphtho[2,3-c]carbazole (7) as a yellow solid; yield: 0.144 g (41%). Further elution of the column (silica gel, 1% EtOAc–hexane) gave 5-hexyl-5H-naphtho[2,3-b]carbazole (8) as a yellow solid; yield: 0.127 g (36%). 7 Mp 104–106 °C (Lit.^4c 104 °C). ¹H NMR (300 MHz, CDCl₃): δ = 9.22 (s, 1 H), 8.74 (d, J = 7.2 Hz, 1 H), 8.51 (s, 1 H), 8.15 (d, J = 8.4 Hz, 1 H), 8.05–7.95 (m, 2 H), 7.62 (d, J = 9.3 Hz, 1 H), 7.57–7.50 (m, 2 H), 7.49–7.44 (m, 3 H), 4.38 (t, J = 6.9 Hz, 2 H, CH₂), 1.88 (t, J = 6.9 Hz, 2 H, CH₂), 1.30–1.25 (m, 6 H, CH₂), 0.87–0.82 (m, 3 H, CH₃). ¹³C NMR (75.4 MHz, CDCl₃): δ = 138.8, 137.3, 132.5, 129.6, 128.7, 128.3, 128.0, 127.9 (2 C), 125.7, 124.3, 123.9, 123.5, 121.8, 120.7, 120.4, 120.1, 113.2, 112.4, 109.6, 43.2, 31.6, 29.8, 27.0, 22.6, 14.0. DEPT-135 NMR (75.4 MHz, CDCl₃): δ = 128.3, 128.0, 127.9 (2 C), 125.7, 124.3, 123.5, 121.8, 120.7, 120.1, 112.4, 109.6, 43.2, 31.6, 29.8, 27.0, 22.6, 14.0. HRMS (EI): m/z [M⁺] calcd for C₂₆H₂₅N: 351.1987; found: 351.1980. 8 Mp 124–126 °C (Lit.^4c 122–124 °C). ¹H NMR (300 MHz, CDCl₃): δ = 8.73 (s, 1 H), 8.66 (s, 1 H), 8.54 (s, 1 H), 8.23 (d, J = 7.5 Hz, 1 H), 8.02 (t, J = 8.9 Hz, 2 H), 7.78 (s, 1 H), 7.54 (t, J = 7.7 Hz, 1 H), 7.44 (t, J = 6.4 Hz, 2 H), 7.35 (t, J = 7.4 Hz, 1 H), 7.24–7.22 (m, 1 H), 4.32 (t, J = 7.4 Hz, 2 H, CH₂), 1.95 (t, J = 6.8 Hz, 2 H, CH₂), 1.51–1.38 (m, 2 H, CH₂), 1.36–1.25 (m, 4 H, CH₃), 0.88 (t, J = 6.9 Hz, 3 H, CH₃). ¹³C NMR (75.4 MHz, CDCl₃): δ = 144.2, 141.0, 131.4 (2 C), 129.6, 128.2, 127.9, 127.6, 127.6, 127.0, 126.7, 124.9, 124.1, 123.8, 122.8, 121.2, 118.8, 118.6, 108.0, 101.2, 43.3, 31.7, 28.3, 27.1, 22.6, 14.0. DEPT-135 NMR (75.4 MHz, CDCl₃): δ = 128.2, 127.9, 127.6, 126.7, 124.9, 124.1, 123.8, 121.2, 118.8, 118.6, 108.0, 101.2, 43.3, 31.7, 28.3, 27.1, 22.6, 14.0. HRMS (EI): m/z [M⁺] calcd for C₂₆H₂₅N: 351.1987; found: 351.1979. Anthra[2,1-b]benzo[d]thiophene (11); Typical Procedure 57% aq HI (2.37 mL, 18.98 mmol) and red phosphorus (0.31 g, 10.1 mmol) were added to a solution of phthalide 13 (0.4 g, 1.26 mmol) in glacial AcOH (30 mL), and the mixture was refluxed for 12 h. After workup similar to that for 7, column chromatography (silica gel, 1% EtOAc–hexane) gave anthra[2,1-b]benzo[d]-thiophene 11 as a pale green solid; yield: 0.307 g (90%); mp 168 °C (Lit.^4c 168–170 °C). ¹H NMR (300 MHz, CDCl₃): δ = 9.40 (s, 1 H), 8.95 (d, J = 8.4 Hz, 1 H), 8.47 (s, 1 H), 8.11 (d, J = 8.1 Hz, 1 H), 7.99–7.90 (m, 3 H), 7.75 (d, J = 9.0 Hz, 1 H), 7.60 (t, J = 7.7 Hz, 1 H), 7.53–7.42 (m, 3 H). ¹³C NMR (75.4 MHz, CDCl₃): δ = 139.7, 138.5, 137.1, 132.3, 130.7, 130.6, 128.9, 128.5, 128.4, 128.2, 128.0, 127.9, 126.1, 125.5, 125.1, 125.0, 124.5, 123.3, 121.7, 120.9. DEPT-135 (75.4 MHz, CDCl₃): δ = 128.5, 128.4, 128.0 (2C), 126.1, 125.6, 125.1, 125.0, 124.5, 123.3, 121.7, 121.0. HRMS (EI): m/z [M⁺] calcd for C₂₀H₁₂S: 284.0660; found: 284.0654.