Oxidative Cleavage of 1,3-Disubstituted Benzo[c]furans with Activated Manganese­ Dioxide: A Facile Preparation of 1,2-Di(het)aroylbenzenes

Abstract

Manganese dioxide mediated oxidative cleavage of 1,3-disubstituted benzo[c]furans in dichloromethane at room temperature gave good yields of 1,2-di(het)aroylbenzenes.

Key words

heterocycles - polycycles - diketones - ring opening - ­oxidation - manganese dioxide

• References and Notes

• 1a Lorcy D, Cava MP. Adv. Mater. (Weinheim, Ger.) 1992; 4: 562
• 1b Bäuerle P, Götz G, Emerle P, Port H. Adv. Mater. (Weinheim, Ger.) 1992; 4: 564
• 1c Musinanni S, Ferraris JP. J. Chem. Soc., Chem. Commun. 1993; 172
• 2a Kiebooms RH. L, Adriaensens PJ. A, Vanderzande DJ. N, Gelan JM. J. V. J. Org. Chem. 1997; 62: 1473
• 2b Mohanakrishnan AK, Lakshmikantham MV, McDougal CD, Cava MP, Baldwin JW, Metzger RM. J. Org. Chem. 1998; 63: 3105
• 2c Amaladass P, Arul Clement J, Mohanakrishnan AK. Eur. J. Org. Chem. 2008; 3798
• 3 Meek ST, Nesterov EE, Swager TM. Org. Lett. 2008; 10: 2991
• 4a Sygula A, Sugula R, Rabideau PW. Org. Lett. 2005; 7: 4999
• 4b Rainboldt JE, Miller GP. J. Org. Chem. 2007; 72: 3020
• 4c Chun D, Cheng Y, Wudl F. Angew. Chem. Int. Ed. 2008; 47: 8380
• 4d Paraskar AS, Reddy AR, Patra A, Wijsboom YH, Gidron O, Shimon LJ. W, Leitus G, Bendikov M. Chem. Eur. J. 2008; 14: 10639
• 4e Mohanty AK, Sen SK, Banerjee S. J. Appl. Polym. Sci. 2011; 122: 3038
• 4f Kuninobu Y, Seiki T, Kanamaru S, Nishina Y, Takai K. Org. Lett. 2010; 12: 5287
• 4g Parkhurst RR, Swager TM. J. Am. Chem. Soc. 2012; 134: 15351
• 5a Mohanakrishnan AK, Amaladass P. Tetrahedron Lett. 2005; 46: 7201
• 5b Mohanakrishnan AK, Amaladass P, Senthil Kumar N. Tetrahedron Lett. 2008; 49: 4792
• 5c Amaladass P, Senthil Kumar N, Mohanakrishnan AK. Tetrahedron 2008; 64: 7992
• 5d Senthil Kumar N, Mohanakrishnan AK. Tetrahedron 2010; 66: 5660
• 6 Sivasakthikumaran R, Nandakumar M, Mohanakrishnan AK. J. Org. Chem. 2012; 77: 9053
• 7a Pierlot C, Nardello V, Schrive J, Matrille C, Barbillat J, Sambret B, Aubry JM. J. Org. Chem. 2002; 67: 2418
• 7b Catir M, Kilic H. Synlett 2003; 1180
• 7c Matsumoto M, Yamada M, Watanabe N. Chem. Commun. 2005; 483
• 7d Sels BF, De Vos DE, Jacobs PA. J. Am. Chem. Soc. 2007; 129: 6916
• 7e Hsu D.-T, Lin C.-H. J. Org. Chem. 2009; 74: 9180
• 7f Hang J, Ghorai P, Finkenstaedt-Quinn SA, Findik I, Sliz E, Kuwata KT, Dussault PH. J. Org. Chem. 2012; 77: 1233
• 8 Nandakumar M, Sivasakthikumaran R, Mohanakrishnan AK. Eur. J. Org. Chem. 2012; 3647
• 9a Letizia JA, Cronin S, Ponce Ortiz R, Facchetti A, Ratner MA, Marks TJ. Chem. Eur. J. 2010; 16: 1911
• 9b Steinberger S, Mishra A, Reinold E, Müller CM, Uhrich C, Pfeiffer M, Bäuerle P. Org. Lett. 2011; 13: 90
• 9c Mei Q, Wang L, Tian B, Tong B, Weng J, Zhang B, Jiang Y, Huang W. Dyes Pigm. 2013; 97: 43
• 9d Liu Y, Zhang F, He C, Wu D, Zhuang X, Xue M, Liu Y, Feng X. Chem. Commun. 2012; 48: 4166
• 9e Harikrishna K, Mukkamala R, Hinkelmann B, Sasse F, Aidhen IS. Eur. J. Org. Chem. 2014; 1066
• 10 Soldatenkov AT, Polyanskii KB, Kolyadina NM, Soldatova SA. Chem. Heterocycl. Compd. (N. Y., NY U. S.) 2009; 45: 633
• 11 Aiello F, Garofolo A, Grande F. Tetrahedron 2010; 66: 274
• 12 Kamimura A, Komatsu H, Moriyama T, Nozaki Y. Tetrahedron 2013; 69: 5968
• 13 Nammalvar B, Fortenberry C, Bunce RA, Lageshetty SK, Ausman KD. Tetrahedron Lett. 2013; 54: 2010
• 14 1,2-Phenylenebis(2-thienylmethanone) (2a); Typical Procedure MnO₂ (0.57 g, 7.09 mmol) was added to a stirred solution of benzo[c]furan 1a (0.5 g, 1.77 mmol) in CH₂Cl₂ (20 mL), and the mixture was stirred at r.t until the benzo[c]furan was consumed (~4 h). The mixture was then filtered through Celite and the residue was washed with CH₂Cl₂ (2 × 10 mL). The combined filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (silica gel; 5% EtOAc–hexane) to give a brown solid; yield: 0.48 g (92%); mp 150–152 °C (Lit. see ref. 1b 149–150 °C); IR (KBr): 1623, 1582, 1568, 1514, 1416 cm^–1; ¹H NMR (300 MHz, CDCl₃): δ = 7.66–7.64 (m, 2 H, ArH), 7.58–7.56 (m, 4 H, ArH), 7.39–7.38 (m, 2 H, ArH), 6.99–6.96 (m, 2 H, ArH); ¹³C NMR (75 MHz, CDCl₃): δ = 188.3, 144.0, 139.4, 135.1, 135.0, 130.6, 129.2, 128.1; DEPT-135 (75 MHz, CDCl₃): δ = 135.2, 135.0, 130.6, 129.2, 128.1; HRMS (EI): m/z [M⁺] calcd for C₁₆H₁₀O₂S₂: 298.0122; found: 298.0121.