RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2015; 47(10): 1447-1454
DOI: 10.1055/s-0034-1380278
DOI: 10.1055/s-0034-1380278
paper
An Efficient, Mild, Solvent-Free, One-Pot Three-Component Mannich Reaction Catalyzed by (C4H12N2)2[BiCl6]Cl·H2O
Autoren
Weitere Informationen
Publikationsverlauf
Received: 18. November 2014
Accepted after revision: 06. Februar 2015
Publikationsdatum:
06. März 2015 (online)
Abstract
An efficient and practical method for the one-pot Mannich reaction of aromatic ketones with aldehydes and amines at room temperature has been developed under solvent-free conditions catalyzed by (C4H12N2)2[BiCl6]Cl·H2O (3 mol%). The catalyst may also be recycled multiple times by simple isolation protocols without compromising the catalytic efficiency.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380278.
- Supporting Information (PDF) (opens in new window)
-
References
- 1a Tanaka K, Tada F. Chem. Rev. 2000; 100: 1025
- 1b Sheldon RA. Green Chem. 2005; 7: 267
- 1c Wang GW, Miao CB. Green Chem. 2006; 8: 1080
- 2a Liu M, Sibi MP. Tetrahedron 2002; 58: 7991
- 2b Evans GB, Furneaux RH, Tyler PC, Schramm VL. Org. Lett. 2003; 5: 3639
- 2c Suginome M, Uehlin L, Murakami M. J. Am. Chem. Soc. 2004; 126: 13196
- 2d Mandloi D, Joshi S, Khadikarc PV, Khosla N. Bioorg. Med. Chem. Lett. 2005; 15: 405
- 2e Simplício AL, Clancy JM, Gilmer JF. Int. J. Pharm. 2007; 336: 208
- 2f Kallstrom S, Leino R. Bioorg. Med. Chem. 2008; 16: 601
- 3 Danishefsky SJ, Chackalamannil S, Harrison P, Silvestri M, Cole P. J. Am. Chem. Soc. 1985; 107: 2474
- 4 Manabe K, Mori Y, Kobayashi S. Tetrahedron 2001; 57: 2537
- 5a Wang R, Li BG, Huang TK, Shi L, Lu XX. Tetrahedron Lett. 2007; 48: 2071
- 5b Wang M, Song Z, Wan X, Zhao S. Monatsh. Chem. 2009; 140: 1205
- 6a Hao WJ, Jiang B, Tu SJ, Cao XD. Org. Biomol. Chem. 2009; 7: 1410
- 6b Wu H, Chen X, Wan Y, Ye L, Xin H, Xu H, Yue C, Pang L, Ma R, Shi D. Tetrahedron Lett. 2009; 50: 1062
- 7a Sahoo S, Joseph T, Halligudi SB. J. Mol. Catal. A: Chem. 2006; 244: 179
- 7b Rafiee E, Eavani S. Green Chem. 2011; 13: 2116
- 7c Kundu K, Nayak SK. RSC Adv. 2012; 2: 480
- 8 Giray ES, Chiappe C, Tunal Z, Rajamani S. RSC Adv. 2011; 1: 761
- 9a Hua R. Curr. Org. Synth. 2008; 5: 1
- 9b Herndon JW. Coord. Chem. Rev. 2009; 253: 1517
- 9c Qin HB, Yamagiwa N, Matsunaga S. Angew. Chem. Int. Ed. 2007; 46: 409
- 9d Dostal L, Novak P, Jambor R, Ruzicka A, Cisarova I, Jirasko R, Holecek J. Organometallics 2007; 26: 2911
- 10 Lu HF, Sun LL. Tetrahedron Lett. 2012; 53: 4267
- 11a Lu HF, Zhou JT, Cheng HL, Sun LL, Yang FF, Wu RZ, Gao YH, Luo ZB. Tetrahedron 2013; 69: 11174
- 11b Gao YH, Liu XJ, Sun LL. Acta Crystallogr., Sect. E 2011; 67: 1688
- 12a Jafari AA, Moradgholi F, Tamaddon F. Eur. J. Org. Chem. 2009; 1249
- 12b Kozlov NG, Basalaeva LI. Russ. J. Gen. Chem. 2004; 74: 926
- 12c Boglio C, Lemière G, Hasenknopf B, Thorimbert S, Lacôte E, Malacria M. Angew. Chem. Int. Ed. 2006; 45: 3325
- 12d Ollevier T, Nadeau E. J. Org. Chem. 2004; 69: 9292
- 12e Loh TP, Liung SB. K. W, Tan KL, Wei LL. Tetrahedron 2000; 56: 3227
- 12f Wu H, Shen Y, Fan LY, Wan Y, Zhang P, Chen CF, Wang WX. Tetrahedron 2007; 63: 2404
- 12g Li H, Zeng HY, Shao HW. Tetrahedron Lett. 2009; 50: 6858
- 12h Zeng H, Li H, Shao H. Ultrason. Sonochem. 2009; 16: 758
- 12i Moutou JL, Schmitt M, Wermuth CG, Bourguignon JJ. Tetrahedron Lett. 1994; 35: 6883
- 12j Rafiee E, Eavani S, Nejad FK, Joshaghani M. Tetrahedron 2010; 66: 6860
- 12k Suginome M, Uehlin L, Yamamoto A. Org. Lett. 2004; 6: 1167