Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(19): 2719-2726
DOI: 10.1055/s-0033-1339515
DOI: 10.1055/s-0033-1339515
paper
Highly Efficient Aluminum Trichloride Catalyzed Michael Addition of Indoles and Pyrroles to Maleimides
Further Information
Publication History
Received: 09 May 2013
Accepted after revision: 11 July 2013
Publication Date:
06 August 2013 (online)
Abstract
A highly efficient synthetic strategy for Michael addition of indoles and pyrroles to maleimides has been developed using the Lewis acids zinc chloride or aluminum trichloride as the catalyst. The reactions generated 3-substituted indoles and 2-substituted pyrroles in high yields with excellent regioselectivity in the presence of a catalytic amount of zinc chloride or aluminum trichloride under mild reaction conditions. The method is simple, efficient, and practical.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Kochanowska-Karamyan AJ, Hamann MT. Chem. Rev. 2010; 110: 4489
- 1b Gupta L, Talwar A, Chauhan PM. S. Curr. Med. Chem. 2007; 14: 1789
- 1c Gul W, Hamann MT. Life Sci. 2005; 78: 442
- 1d Karchava AV, Melkonyan FS, Yurovskaya MA. Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 2012; 48: 391
- 1e Trost BM, Brennan MK. Synthesis 2009; 3003
- 1f Li SM. Nat. Prod. Rep. 2010; 27: 57
- 1g Saracoglu N. Top. Heterocycl. Chem. 2007; 11: 1
- 2a Mahboobi S, Eichhorn E, Popp A, Sellmer A, Elz S, Moellmann U. Eur. J. Med. Chem. 2006; 41: 176
- 2b Conchon E, Anizon F, Aboab B, Golsteyn RM, Leonce S, Pfeiffer B, Prudhomme M. Eur. J. Med. Chem. 2008; 43: 282
- 2c Conchon E, Anizon F, Aboab B, Prudhomme M. J. Med. Chem. 2007; 50: 4669
- 2d Schmoele A.-C, Brennfuehrer A, Karapetyan G, Jaster R, Pews-Davtyan A, Huebner R, Ortinau S, Beller M, Rolfs A, Frech MJ. Bioorg. Med. Chem. 2010; 18: 6785
- 2e Zhao SY, Yang YW, Zhang HQ, Yue Y, Fan M. Arch. Pharmacal. Res. 2011; 34: 519
- 3a Lee YS, Lin Z, Chen YY, Liu CY, Chow TJ. Org. Electron. 2010; 11: 604
- 3b Murakami T, Nakazono M, Kondorskiy A, Ishida T, Nanbu S. Phys. Chem. Chem. Phys. 2012; 14: 11546
- 3c Pews-Davtyan A, Tillack A, Ortinau S, Rolfs A, Beller M. Org. Biomol. Chem. 2008; 6: 992
- 3d Nakazono M, Nanbu S, Uesaki A, Kuwano R, Kashiwabara M, Zaitsu K. Org. Lett. 2007; 9: 3583
- 4a Henon H, Messaoudi S, Hugon B, Anizon F, Pfeiffer B, Prudhomme M. Tetrahedron 2005; 61: 5599
- 4b Cho YS, Whitehead L, Li J, Chen CH, Jiang L, Vogtle M, Francotte E, Richert P, Wagner T, Traebert M, Lu Q, Cao X. J. Med. Chem. 2010; 53: 2952
- 5 Bergman J, Desarbre E, Koch E. Tetrahedron 1999; 55: 2363
- 6a Zeng M, You SL. Synlett 2010; 1289
- 6b Marques-Lopez E, Diez-Martinez A, Merino P, Herrera RP. Curr. Org. Chem. 2009; 13: 1585
- 6c Bandini M, Eichholzer A, Umani-Ronchi A. Mini-Rev. Org. Chem. 2007; 4: 115
- 6d Bartoli G, Bencivenni G, Dalpozzo R. Chem. Soc. Rev. 2010; 39: 4449
- 6e Wang J, Li P, Choy PY, Chan AS. C, Kwong FY. ChemCatChem 2012; 4: 917
- 6f Lee HJ, Kim DY. Synlett 2012; 23: 1629
- 7a Liu P, Chen W, Ren K, Wang L. Chin. J. Chem. 2010; 28: 2399
- 7b Bandini M, Melchiorre P, Melloni A, Umani-Ronchi A. Synthesis 2002; 1110
- 8 Bartoli G, Bartolacci M, Bosco M, Foglia G, Giuliani A, Marcantoni E, Sambri L, Torregiani E. J. Org. Chem. 2003; 68: 4594
- 9 Lu SF, Du DM, Xu J. Org. Lett. 2006; 8: 2115
- 10 Kumar V, Kaur S, Kumar S. Tetrahedron Lett. 2006; 47: 7001
- 11 Arcadi A, Bianchi G, Chiarini M, Anniballe GD, Marinelli F. Synlett 2004; 944
- 12 Tabatabaeian K, Mamaghani M, Mahmoodi NO, Khorshidi A. J. Mol. Catal. A: Chem. 2007; 270: 112
- 13 Ji X, Tong HB, Yuan Y. Synth. Commun. 2011; 41: 372
- 14 Subramanian T, Kumarraja M, Pitchumani K. J. Mol. Catal. A: Chem. 2012; 363-364: 115
- 15 Srivastava N, Banik B. J. Org. Chem. 2003; 68: 2109
- 16a Lin C, Hsu J, Sastry MN. V, Fang H, Tu Z, Liu JT, Ching-Fa Y. Tetrahedron 2005; 61: 11751
- 16b Wang S, Ji S, Loh T. Synlett 2003; 2377
- 17a Dubois L, Acher FC, McCort-Tranchepain I. Synlett 2012; 23: 791
- 17b De Rosa M, Soriente A. Tetrahedron 2010; 66: 2981
- 17c Pessoa-Mahana H, Gonzalez M, Gonzalez M, Pessoa-Mahana D, Araya-Maturana R, Ron N, Saitz C. ARKIVOC 2009; 316
- 18a Li WJ, Lin XF, Wang J, Li GL, Wang YG. Synlett 2005; 2003
- 18b Shen W, Wang L, Tang J, Qian Z, Tong X. Chin. J. Chem. 2010; 28: 443
- 19a Shiri M, Zolfigol MA, Ayazi-Nasrabadi R. Tetrahedron Lett. 2010; 51: 264
- 19b Gupta P, Paul S. J. Mol. Catal. A: Chem. 2012; 352: 75
- 19c Ismail NS. M, El Dine RS, Hattori M, Takahashi K, Ihara M. Bioorg. Med. Chem. 2008; 16: 7877
- 19d Horikawa N, Obora Y, Ishii Y. Synlett 2011; 857
- 19e Zhang Y, Dou Q, Dai L, Wang X, Chen Y. RSC Adv. 2012; 2: 8979
- 20a Davis PD, Hill CH, Lawton G, Nixon JS, Wilkinson SE, Hurst SA, Keech EK, Turner SE. J. Med. Chem. 1992; 35: 177
- 20b Slater MJ, Cockerill S, Baxter R, Bonser RW, Gohil K, Gowrie C, Robinson JE, Littler E, Parry N, Randall R, Snowden W. Bioorg. Med. Chem. 1999; 7: 1067
- 21 Kaletas BK, Joshi HC, Van der Zwan G, Fanti M, Zerbetto F, Goubitz K, De Cola L, Konig B, Williams RM. J. Phys. Chem. A 2005; 109: 9443
- 22 Macor JE, Blank DH, Ryan K, Post RJ. Synthesis 1997; 443
- 23 Bogza SL, Kobrakov KI, Zubritskii MY, Suikov SY, Dulenko VI. Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 1997; 33: 74
- 24 Julia M, Bagot J. Bull. Soc. Chim. Fr. 1964; 1924
- 25 Henon H, Anizon F, Kucharczyk N, Loynel A, Casara P, Pfeiffer B, Prudhomme M. Synthesis 2006; 711