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; Arasambattu K. Mohanakrishnan

doi:10.1055/s-0036-1588337

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(03): 362-370
DOI: 10.1055/s-0036-1588337

letter

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

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Abstract

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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

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Referenzen

References and Notes

1a Heckmann A, Lambert C. Angew. Chem. Int. Ed. 2012; 51: 326
1b Heimel G, Salzmann I, Duhm S, Koch N. Chem. Mater. 2011; 23: 359
1c Lo S.-C, Burn PL. Chem. Rev. 2007; 107: 1097
1d Anthony JE. Chem. Rev. 2006; 106: 5028

2a Kobayashi K, Masu H, Shuto A, Yamaguchi K. Chem. Mater. 2005; 17: 6666
2b Nerungsi C, Wanitchang P, Sahasithiwat S, Sadorn K, Kerdcharoen T, Thongpanchang T. Tetrahedron Lett. 2010; 51: 6392

3a Bradsher CK. Chem. Rev. 1987; 87: 1277
3b Mamada M, Minamiki M, Katagiri H, Tokito S. Org. Lett. 2012; 14: 4062
3c Okamoto K, Kawamura T, Sone M, Ogino K. Liq. Cryst. 2007; 34: 1001
3d Surya Prakash GK, Panja C, Shakhmin A, Shah E, Mathew T, Olah GA. J. Org. Chem. 2009; 74: 8659
3e Sereviĉius T, Adomėnas P, Adomėnienė O, Rimkus R, Jankauskas V, Gruodis A, Kazlauskas K, Jurŝėnas S. Dyes Pigm. 2013; 98: 304

4a Kuninobu Y, Tatsuzaki T, Matsuki T, Takai K. J. Org. Chem. 2011; 76: 7005
4b Yu X, Lu X. Adv. Synth. Catal. 2011; 353: 569
4c Rafiq SM, Sivasakthikumaran R, Karunakaran J, Mohanakrishnan AK. Eur. J. Org. Chem. 2015; 5099

5 Coffey S, Boyd V. J. Chem. Soc. 1954; 2468
6 Manning WB, Muechik GM, Tomaszweski JE. J. Org. Chem. 1979; 44: 699

7a Bradsher CK. Chem. Rev. 1946; 38: 447
7b Fitzgerald JF, Drysdale NE, Olofson RA. J. Org. Chem. 1992; 57: 7122

8 Trahanovsky WS, Tunkel JL, Thoen JC, Wang YJ. J. Org. Chem. 1996; 60: 8407

9a Kodomari M, Nagamatsu M, Akaike M, Aoyama T. Tetrahedron Lett. 2008; 49: 2537
9b Yamato T, Sakaue N, Shinoda N, Matsuo K. J. Chem. Soc., Perkin Trans. 1 1997; 1193
9c Ahmed M, Ashby J, Ayad M, Meth-Cohn O. J. Chem. Soc., Perkin Trans. 1 1973; 1099

10a Kotha S, Misra S, Halder S. Tetrahedron 2008; 64: 10775
10b Yasukawa T, Satoh T, Miura M, Nomura M. J. Am. Chem. Soc. 2002; 124: 12680
10c Zou Y, Young DD, Cruz-Montanez A, Deiters A. Org. Lett. 2008; 10: 4661
10d Takahashi T, Li S, Huang W, Kong F, Nakajima K, Shen B, Ohe T, Kanno K. J. Org. Chem. 2006; 71: 7967

11a Graebe C, Liebermann C. Justus Liebigs Ann. Chem., Suppl. 1870; 7: 287
11b Liebermann C, Topf A. Chem. Ber. 1876; 9: 1201
11c Liebermann C. Justus Liebigs Ann. Chem. 1882; 212: 1

12a Harvey RG, Goh SH, Cortez C. J. Am. Chem. Soc. 1975; 97: 3468
12b Harvey RG, Fu PP In Polycyclic Hydrocarbons and Cancer: Environment, Chemistry, and Metabolism . Vol. 1, Chap. 6. Gelboin HV, Ts’o PO. P. Academic Press; New York: 1978: 133

13a Criswell TR, Klanderman BH. J. Org. Chem. 1974; 39: 770
13b Cho H, Harvey RG. J. Chem. Soc., Perkin Trans. 1 1976; 836

14 Sanchorawala CJ, Subba Rao BC, Unni MK, Venkataraman K. Indian J. Chem. 1963; 1: 19
15 Bapat DS, Subba Rao BC, Unni MK, Venkataraman K. Tetrahedron Lett. 1960; (26) : 15
16 Clar E. Polycyclic Hydrocarbons . Vols. I and II. Academic; New York: 1964
17 Gilman H, Diehl J. J. Org. Chem. 1961; 26: 4817

18a Platt KL, Oesch F. J. Org. Chem. 1981; 46: 2601
18b Harvey RG, Leyba C, Konieczny M, Fu PP, Sukumaran KB. J. Org. Chem. 1978; 43: 3423

19a Graebe C, Liebermann C. Justus Liebigs Ann. Chem. 1870; 155: 257
19b Liebermann C. Justus Liebigs Ann. Chem. 1871; 158: 299
19c Schmidt E. J. Prakt. Chem. 1874; 9: 241

20a Meakins GD, Swindells R. J. Chem. Soc. 1959; 1044
20b Ho T.-L, Wong CM. Synthesis 1975; 161

21 Guerrero TH, Deulofeu V. Chem. Ber. 1937; 70: 947
22 Giebe G. Chem. Ber. 1896; 29: 2533
23 Clar E. Polycyclic Hydrocarbons . Vol. 1. Academic Press; New York: 1964: 171
24 Miller GP, Briggs J. Org. Lett. 2003; 5: 4203
25 Aprahamian I, Preda DV, Bancu M, Belanger AP, Sheradsky T, Scott LT, Rabinovitz M. J. Org. Chem. 2006; 71: 290
26 Sivasakthikumaran R, Rafiq SM, Sankar E, Mohanakrishnan AK. Eur. J. Org. Chem. 2015; 7816
27 Kotha S, Ghosh AK. Synlett 2002; 451
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.

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