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.

Key words： carbonylative cyclization reactions; isoindole-1,3-dinones; homogeneous catalysis; dppf

Acknowledgements

The author (M. V. Khedkar) is greatly thankful to UGC (University Grant Commission, India) for providing Junior Research Fellowship.

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