Facile synthesis of isoindoline-1,3-diones by palladium-catalyzed carbonylative cyclization of o-bromobenzoic acid and primary amines

Abstract

A facile method for the carbonylative cyclization of o-bromobenzoic acid with primary amine using Pd(OAC)₂ as a metal precursor and 1,1'-bis(diphenylphosphino)ferrocene (dppf) as a ligand has been developed. The effect of various reaction parameters such as ligand, solvent, base, time and temperature on this cyclization was studied. The optimized protocol was used for a wide variety of substituted aryl amines with different steric and electronic properties, affording the corresponding isoindoline-1,3-diones in good to excellent yields under atmospheric pressure of carbon monoxide at 100°C within 10 h using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a base. The reaction system finds attractive alternative to the conventional multistep synthetic process and thus represents an effective utilization of carbonylative protocol for synthesis of valuable chemicals.

Keywords

carbonylative cyclization reactions / isoindole-1,3-dinones / homogeneous catalysis / dppf

References

[1] Ashcroft A T, Cheetham A K, Green M L H, Vernon P D F. Partial oxidation of methane to synthesis gas using carbon dioxide. Nature, 1991, 352(6332): 225–226

[2] Trost B M. The atom economy--a search for synthetic efficiency. Science, 1991, 254(5037): 1471–1477

[3] Abramovitch R A, Shinkai I, Mavunkel B J, More K M, O'Connor S, Ooi G H, Pennington W T, Srinivasan P C, Stowers J R. New ring systems from 1,2-benzisothiazole-1,1-dioxides and related compounds. Tetrahedron, 1996, 52(9): 3339–3354

[4] Wood J L, Stoltz B M, Goodman S N. Total Synthesis of (+)-RK-286c, (+)-MLR-52, (+)-staurosporine, and (+)-K252a. Journal of the American Chemical Society, 1996, 118(43): 10656–10657

[5] Hall I H, Chapman J M Jr, Wong O T. The cytotoxic activity of cyclic imido alkyl ethers, thioethers, sulfoxides, sulfones and related derivatives. Anti-Cancer Drugs, 1994, 5(1): 75–82

[6] Makonkawkeyoon S, Limson-Pobre R N R, Moreira A L, Schauf V, Kaplan G. Thalidomide inhibits the replication of human immunodeficiency virus type 1. Proceedings of the National Academy of Sciences of the United States of America, 1993, 90(13): 5974–5978

[7] Figg W D, Raje S, Bauer K S, Tompkins A, Venzon D, Bergan R, Chen A, Hamilton M, Pluda J, Reed E. Pharmacokinetics of thalidomide in an elderly prostate cancer population. Journal of Pharmaceutical Sciences, 1999, 88(1): 121–125

[8] Atra E, Sato E I. Treatment of the cutaneous lesions of systemic lupus erythematosus with thalidomide. Clinical and Experimental Rheumatology, 1993, 11(5): 487–493

[9] Ochonisky S, Verroust J, Bastuji-Garin S, Gherardi R, Revuz J. Thalidomide neuropathy incidence and clinico-electrophysiologic findings in 42 patients. Archives of Dermatology, 1994, 130(1): 66–69

[10] Miyachi H, Azuma A, Ogasawara A, Uchimura E, Watanabe N, Kobayashi Y, Kato F, Kato M, Hashimoto Y. Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity. Journal of Medicinal Chemistry, 1997, 40(18): 2858–2865

[11] Li X, Zhan J, Li Y. Facile syntheses and characterization of hyperbranched poly(ester-amide)s from commercially available aliphatic carboxylic anhydride and multihydroxyl primary amine. Macromolecules, 2004, 37(20): 7584–7594

[12] Hellwinkel D, Lenz R, Lämmerzahl F. Heterocyclic syntheses via carbanionically induced rearrangement reactions. Tetrahedron, 1983, 39(12): 2073–2084

[13] Mori M, Chiba K, Ohta N, Ban Y. A novel synthesis of cyclic imides and quinolone by use of paliadium catalyzed carbonylation. Heterocycles, 1979, 13(1): 329–332

[14] Perry R J, Turner S R. Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines. Journal of Organic Chemistry, 1991, 56(23): 6573–6579

[15] Taká A, Acscs P, Kollar L. Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene. Tetrahedron, 2008, 64(6): 983–987

[16] Worlikar S A, Larock R C. Palladium-catalyzed one-step synthesis of isoindole-1,3-diones by carbonylative cyclization of o-halobenzoates and primary amines. Journal of Organic Chemistry, 2008, 73(18): 7175–7180

[17] Khedkar M V, Khan S R, Sawant D N, Bagal D B, Bhanage B M. Palladium on carbon: an efficient, heterogeneous and reusable catalytic system for carbonylative synthesis of N-substituted phthalimides. Advanced Synthesis & Catalysis, 2011, 353(18): 3415–3422

[18] Khedkar M V, Khan S R, Dhake K P, Bhanage B M. Carbonylative cyclization of o-halobenzoic acids for synthesis of N-substituted phthalimides using polymer supported palladium N-heterocyclic carbene as an efficient, heterogeneous and reusable catalyst. Synthesis, 2012, 44(16): 2623–2629

[19] Cao H, Alper H. Palladium-catalyzed double carbonylation reactions of o-dihaloarenes with amines in phosphonium salt ionic liquids. Organic Letters, 2010, 12(18): 4126–4129

[20] Khedkar M V, Tambade P J, Qureshi Z S, Bhanage B M. Pd/C: an efficient, heterogeneous and reusable catalyst for phosphane-free carbonylative suzuki coupling reactions of aryl and heteroaryl iodides. European Journal of Organic Chemistry, 2010, 2010(36): 6981–6986

[21] Gadge S T, Khedkar M V, Lanke S R, Bhanage B M. Oxidative aminocarbonylation of terminal alkynes for the synthesis of alk-2-ynamides by using palladium-on-carbon as efficient, heterogeneous, phosphine-free, and reusable catalyst. Advanced Synthesis & Catalysis, 2012, 354(10): 2049–2056

[22] Khedkar M V, Sasaki T, Bhanage B M. Immobilized palladium metal containing ionic liquid catalyzed alkoxycarbonylation, phenoxycarbonylation and aminocarbonylation reactions. ACS Catalysis, 2013: 287–293

[23] Qureshi Z S, Revankar S A, Khedkar M V, Bhanage B M. Aminocarbonylation of aryl iodides with primary and secondary amines in aqueous medium using polymer supported palladium-N-heterocyclic carbene complex as an efficient and heterogeneous recyclable catalyst. Catalysis Today, 2012, 198(1): 148–153

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