Catalyst-Free One-Pot Access to 3-Pyrazolylisoindolinone Derivatives

Abstract

A series of 3-pyrazolylisoindolinone derivatives were synthesized by a concise, efficient, three-component reaction of a 2-formylbenzoic acid, a primary amine (or ammonium hydroxide), and a pyrazolone under catalyst-free conditions. This novel procedure has the advantages of easy handling, mild reaction conditions, and a wide substrate scope, and can be performed as a one-pot operation.

Key words

heterocycles - polycycles - amines - multicomponent reactions - catalyst-free

• References

• 1a Dömling A. Curr. Opin. Chem. Biol. 2002; 6: 306
• 1b Akritopoulou-Zanze I. Curr. Opin. Chem. Biol. 2008; 12: 324
• 2a Kato Y, Takemoto M, Achiwa K. Chem. Pharm. Bull. 1993; 41: 2003
• 2b Heaney H, Shuhaibar KF. Synlett 1995; 47
• 2c Othman M, Pigeon P, Decroix B. Tetrahedron 1997; 53: 2495
• 2d Boger DL, Lee JK, Goldberg J, Jin Q. J. Org. Chem. 2000; 65: 1467
• 2e Comins DL, Schilling S, Zhang Y. Org. Lett. 2004; 7: 95
• 2f Ghosh U, Bhattacharyya R, Keche A. Tetrahedron 2010; 66: 2148
• 3 Uno M, Ban HS, Nakamura H. Bioorg. Med. Chem. Lett. 2009; 19: 3166
• 4 Takahashi I, Hirano E, Kawakami T, Kitajima H. Heterocycles 1996; 43: 2343
• 5 Muller GW, Chen R, Huang S.-Y, Corral LG, Wong LM, Patterson RT, Chen Y, Kaplan G, Stirling DI. Bioorg. Med. Chem. Lett. 1999; 9: 1625
• 6 Pigeon P, Decroix B. Tetrahedron Lett. 1997; 38: 2985

For studies on 3-substituted isoindolinones, see:
• 7a Wang E.-C, Chen H.-F, Feng P.-K, Lin Y.-L, Hsu M.-K. Tetrahedron Lett. 2002; 43: 9163
• 7b Andryukhova NP, Pozharskaya OA, Golubeva GA, Sviridova LA, Sadovoy AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2009; 45: 672
• 7c Angelin M, Rahm M, Fischer A, Brinck T, Ramström O. J. Org. Chem. 2010; 75: 5882
• 7d Zhu C, Falck JR. Org. Lett. 2011; 13: 1214
• 7e Shacklady-McAtee DM, Dasgupta S, Watson MP. Org. Lett. 2011; 13: 3490
• 7f Wrigglesworth JW, Cox B, Lloyd-Jones GC, Booker-Milburn KI. Org. Lett. 2011; 13: 5326
• 7g Augner D, Gerbino DC, Slavov N, Neudörfl J.-M, Schmalz H.-G. Org. Lett. 2011; 13: 5374
• 7h Shi L.-Y, Hu L, Wang J.-Q, Cao X.-Q, Gu H.-W. Org. Lett. 2012; 14: 1876
• 8a Shen S.-C, Sun X.-W, Lin G.-Q. Green Chem. 2013; 15: 896
• 8b Chen F, Lei M, Hu L. Green Chem. 2014; 16: 2472

For studies on pyrazolones, see:
• 9a Sondhi SM, Sharma VK, Verma RP, Singhal N, Shukla R, Raghubir R, Dubey MP. Synthesis 1999; 878
• 9b Souza FR, Souza VT, Ratzlaff V, Borges LP, Oliveira MR, Bonacorso HG, Zanatta N, Martins MA. P, Mello CF. Eur. J. Pharmacol. 2002; 451: 141
• 9c Braña MF, Gradillas A, Ovalles AG, López B, Acero N, Llinares F, Mingarro DM. Bioorg. Med. Chem. 2006; 14: 9
• 9d Fan X.-S, Zhang X.-Y, Zhou L.-H, Keith KA, Kern ER, Torrence PF. Bioorg. Med. Chem. Lett. 2006; 16: 3224
• 9e Fevig JM, Cacciola J, Buriak JJr, Rossi KA, Knabb RM, Luettgen JM, Wong PC, Bai SA, Wexler RR, Lam PY. S. Bioorg. Med. Chem. Lett. 2006; 16: 3755
• 9f Castagnolo D, De Logu A, Radi M, Bechi B, Manetti F, Magnani M, Supino S, Meleddu R, Chisu L, Botta M. Bioorg. Med. Chem. 2008; 16: 8587
• 9g Venkat Ragavan R, Vijayakumar V, Suchetha Kumari N. Eur. J. Med. Chem. 2009; 44: 3852
• 9h Bashir R, Ovais S, Yaseen S, Hamid H, Alam MS, Samim M, Singh S, Javed K. Bioorg. Med. Chem. Lett. 2011; 21: 4301
• 10a Yu J, Zhou Y, Shen T, Mao W, Chen K, Song Q. J. Chem. Res. 2013; 37: 365
• 10b Yu J, Shen T, Lin Y, Zhou Y, Song Q. Synth. Commun. 2014; 44: 2029
• 10c Che F, Wang Y, Shen T, An X, Song Q. C. R. Chim. 2014; 18: 607
• 10d Shen T, Fu Z, Che F, Dang H, Lin Y, Song Q. Tetrahedron Lett. 2015; 56: 1072
• 11 Motamedi A, Sattari E, Mirzaei P, Armaghan M, Bazgir A. Tetrahedron Lett. 2014; 55: 2366
• 12 Crystallographic data for compound 6a have been deposited with the accession number CCDC 1032129, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: [phone]; E-mail: [e-mail]; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.