Synlett 2017; 28(03): 362-370
DOI: 10.1055/s-0036-1588337
letter
© Georg Thieme Verlag Stuttgart · New York

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

Settu Muhamad Rafiq
Department of Organic Chemistry, School of Chemical Sciences, University of Madras, Guindy Campus, Chennai 600 025, Tamil Nadu, India   Email: mohanakrishnan@unom.ac.in   Email: mohan_67@hotmail.com
,
Arasambattu K. Mohanakrishnan*
Department of Organic Chemistry, School of Chemical Sciences, University of Madras, Guindy Campus, Chennai 600 025, Tamil Nadu, India   Email: mohanakrishnan@unom.ac.in   Email: mohan_67@hotmail.com
› Author Affiliations
Further Information

Publication History

Received: 11 August 2016

Accepted after revision: 29 September 2016

Publication Date:
17 October 2016 (online)


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.

Supporting Information

 
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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.