Palladium-Catalyzed Direct Arylation for the Synthesis of Indeno[2,1-b]-pyrrol-8-ones

Abstract

Treatment of 2-bromophenyl (N-tosylpyrrol-2′-yl)­-ketones with Pd(OAc)₂, Ph₃P, and K₂CO₃ resulted in the formation of indeno[2,1-b]pyrrol-8-ones in moderate to good yields.

Key words

direct arylation - palladium catalyst - acylation - ­indeno[2,1-b]pyrrol-8-one - pyrroles

• References and Notes


For recent reviews, see:
• 1a McGlacken GP, Bateman LM. Chem. Soc. Rev. 2009; 38: 2447
• 1b Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew Chem. Int. Ed. 2009; 48: 5094
• 1c Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
• 2 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
• 3 Negishi E.-I, Liu F In Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998: 1-47
• 4 Schröter S, Stock C, Bach T. Tetrahedron 2005; 61: 2245
• 5 Stanforth SP. Tetrahedron 1998; 54: 263
• 6 Hiyama T In Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998: 421-453
• 7a Qabaja G, Jones GB. Tetrahedron Lett. 2000; 41: 5317
• 7b Kozikowski AP, Ma D. Tetrahedron Lett. 1991; 32: 3317
• 7c Liu T.-P, Liao Y.-X, Xing C.-H, Hu Q.-S. Org. Lett. 2011; 13: 2452
• 7d Campo MA, Larock RC. Org. Lett. 2000; 2: 3675
• 7e Campo MA, Larock RC. J. Org. Chem. 2002; 67: 5616
• 7f Matsuda Y, Kohra S, Katou K, Uemura T, Yamashita K. Heterocycles 2003; 60: 405
• 7g Chernyak N, Tilly D, Li Z, Gevorgyan V. Chem. Commun. 2010; 46: 150
• 7h Romagnoli R, Baraldi PG, Carrion MD, Cara CL, Cruz-Lopez O, Tolomeo M, Grimaudo S, Cristina AD, Pipitone MR, Balzarini J, Zonta N, Brancale A, Hamel E. Bioorg. Med. Chem. 2009; 17: 6862
• 8a Li V.-S, Choi D, Wang Z, Jimenez LS, Tang M.-S, Kohn H. J. Am. Chem. Soc. 1996; 118: 2326
• 8b Perry PJ, Read MA, Davies RT, Gowan SM, Reszka AP, Wood AA, Kelland LR, Neidle S. J. Med. Chem. 1999; 42: 2679
• 8c Greenlee ML, Laub JB, Rouen GP, DiNinno F, Hammond ML, Huber JL, Sundelof JG, Hammond GG. Bioorg. Med. Chem. Lett. 1999; 9: 3225
• 8d Lisowki V, Léonce S, Kraus-Berthier L, Sopková-de Oliveira Santos J, Pierré A, Atassi G, Caignard D.-H, Renard P, Rault S. J. Med. Chem. 2004; 47: 1448
• 8e Gould SJ, Melville CR, Cone MC, Chen J, Carney JR. J. Org. Chem. 1997; 62: 320
• 8f Tierney MT, Grinstaff MW. J. Org. Chem. 2000; 65: 5355
• 9 Song C, Knight DW, Whatton MA. Tetrahedron Lett. 2004; 45: 9573
• 10 A mixture of 2a (210 mg, 0.52 mmol), Pd(OAc)₂ (11 mg, 0.05 mmol), Ph₃P (26 mg 0.10 mmol), and K₂CO₃ (216 mg, 1.56 mmol) in anhyd DMF (11 mL) under N₂ was heated to 120 °C for 9 h and cooled. The mixture was partitioned between EtOAc (60 mL) and H₂O (100 mL). The separated aqueous phase was extracted with EtOAc (3 × 50 mL). The combined organic extracts were washed with brine (150 mL), then dried (Na₂SO₄), filtered, and evaporated. The residue was purified by column chromatography on silica gel (35% EtOAc in PE) to give 1a (68 mg, 78%) as a red solid; mp 205–206 °C. IR: ν_max = 3222, 1690, 1632, 1607, 1509, 1450, 1357, 1319, 1272, 1098 cm^–1. ¹H NMR (300 MHz, DMSO-d ₆): δ = 6.19 (1 H, m), 6.99–7.27 (5 H m), 12.00 (1 H, s). ¹³C NMR (75 MHz, DMSO-d ₆): δ = 103.8, 119.0, 122.6, 126.9, 131.2, 131.7, 133.2, 138.0, 139.1, 142.9, 180.0. ESI-MS: m/z (%) = 192 (100) [M + Na]⁺, 170 (53) [M + H]⁺. HRMS: m/z calcd for C₁₁H₇NNaO: 192.0425; found: 192.0416 [M + Na]⁺.
• 11 Kashulin IA, Nifant’ev IE. J. Org. Chem. 2004; 69: 5476
• 12a Rault S, Lancelot JC, Bouyazza L, Robba M, Quermonne MA, Nammathao B, Louchahi-Raoul J, Marcy R. Eur. J. Med. Chem. 1991; 939
• 12b Rochais C, Dallemagne P, Rault S. Anti-Cancer Agents Med. Chem. 2009; 9: 369
• 12c Diana P, Stagno A, Barraja P, Montalbano A, Carbone A, Parrino B, Cirrincione G. Tetrahedron 2011; 67: 3374
• 13a Aiello F, Garofalo A, Grande F. Tetrahedron Lett. 2010; 51: 6635
• 13b Aiello F, Garofalo A, Grande F. Tetrahedron Lett. 2011; 52: 5824
• 13c Aiello F, Garofalo A, Grande F. Tetrahedron 2010; 66: 274
• 13d Josey AD, Jenner EL. J. Org. Chem. 1962; 27: 2466
• 13e Mazzola VJ, Bernady KF, Franck RW. J. Org. Chem. 1967; 32: 486
• 13f Bailey AS, Scott PW, Vandrevala MH. J. Chem. Soc., Perkin Trans. 1 1980; 97
• 13g Kobayashi K, Himei Y, Fukamachi S, Tanmatsu M, Morikawa O, Konishi H. Tetrahedron 2007; 63: 4356