Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck–Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates

Abstract

For the preparation of compound libraries of Michael acceptors with tunable reactivity toward nuclophilic selenocysteine residue of thioredoxin reductase, a range of 3-arylglutaconic acids were required. The existing methods at the time had limited scope or involved several steps. A hitherto undescribed protocol for direct palladium(II) acetate-catalyzed arylation of glutaconic acid dimethyl ester at position 3 has been developed with a diverse set of arenediazonium tosylates followed by hydrolysis. This generally good-yielding two-step sequence displayed a propensity to deliver E-configured coupling products while compounds mostly featured in the literature were predominantly Z-configured. The possibility for preparing a library of 4-arylpyridine-2,6(1H,3H)-diones has been exemplified.

Key words

arylpent-2-enedioic acids - glutaconic acid - diazonium tosylate - Pd-catalyzed coupling - regiospecificity - ester hydrolysis - imide synthesis

• References

• 1 Address correspondence to this author at the Laboratory of Chemical Pharmacology, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskyi prospekt, Peterhof 198504, Russian Federation.
• 2 Buggle K, Ghogain UN, Nangle M, MacManus P. J. Chem. Soc., Perkin Trans. 1 1983; 1427
• 3 Pednekar SR, Samant SD, Deodhar KD. Heterocycles 1984; 22: 1979
• 4 Pednekar S, Jain AK, Menon KK. Indian J. Heterocycl. Chem. 2004; 14: 1
• 5 Khatri AI, Samant SD. Synthesis 2015; 47: 343
• 6 Zhang B, Zhang J, Peng S, Liu R, Li X, Hou Y, Han X, Fang J. Exp. Opin. Ther. Pat. 2017; 27: 547
• 7 Patel NB, Sharma RD. Synth. Commun. 2013; 43: 1250
• 8 Reich HJ, Hondal RJ. ACS Chem. Biol. 2016; 11: 821
• 9a Sanin AV, Nenajdenko VG, Kuzʼmin VS, Balenkova ES. J. Org. Chem. 1996; 61: 1986
• 9b Chen J, Meng S, Wang L, Tang H, Huang Y. Chem. Sci. 2015; 6: 4184
• 9c Chen W, Jing Z, Chin KF, Qiao B, Zhao Y, Yan L, Tan C.-H, Jiang Z. Adv. Synth. Catal. 2014; 356: 1292
• 9d Wang Y.-F, Wu S, Karmaker PG, Sohail M, Wang Q, Chen F.-X. Synthesis 2015; 47: 1147
• 10 SciFinder search performed on December 23, 2018.
• 11 Peet NP, Sunder S. Heterocycles 1986; 24: 393
• 12 Balazs L, Kadas I, Tõke L. Tetrahedron Lett. 2000; 41: 7583
• 13 Jagtap S. Catalysts 2017; 7: 267
• 14 Roglans A, Pla-Quintana A, Moreno-Manas M. Chem. Rev. 2006; 106: 4622

Selected examples:
• 15a Kamble RB, Devalankar D, Suryavanshi G. New J. Chem. 2018; 42: 10414
• 15b Pastre JC, Correia CR. D. Adv. Synth. Catal. 2009; 351: 1217
• 15c Kalkhambkar RG, Laali KK. Tetrahedron Lett. 2011; 52: 1733
• 15d Prediger P, da Silva AR, Correia CR. D. Tetrahedron 2014; 70: 3333
• 15e Pastre JC, Correia CR. D. Org. Lett. 2006; 8: 1657
• 16 Kikukawa K, Nagira K, Wada F, Matsuda T. Tetrahedron 1981; 37: 34
• 17 Bräse S, de Meijere A. Cross-Coupling of Organyl Halides with Alkenes – The Heck Reaction. In Metal-Catalyzed Cross-Coupling Reactions and More. de Meijere A, Bräse S, Oestreich M. Wiley-VCH; Weinheim: 2014: 533-664
• 18 Filimonov VD, Trusova M, Postnikov P, Krasnokutskaya EA, Lee YM, Hawng HY, Kim H, Chi K.-W. Org. Lett. 2008; 10: 3961
• 19 Kutonova KV, Trusova ME, Stankevich AV, Postnikov PS, Filimonov VD. Beilstein J. Org. Chem. 2015; 11. 358
• 20 Khatri AI, Samant SD. RSC Adv. 2015; 5. 2009
• 21 Butera J, Bagli J, Doubleday W, Humber L, Treasurywala A, Loughney D, Sestanj K, Millen J, Sredy J. J. Med. Chem. 1989; 32: 757
• 22a Joshi GW, Samant SD, Deodhar KD, Kulkarni RA. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1981; 20: 1050
• 22b Hattori K, Kurihara N, Iwaki T, Inoue T, Akiyama T, Hasegawa Y. PCT Int. Appl. WO2013002357, 2013 ; Chem. Abstr. 2013, 158, 158456.