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Synlett 2013; 24(14): 1791-1794
DOI: 10.1055/s-0033-1339294
DOI: 10.1055/s-0033-1339294
letter
Improved Catalyst-Free Synthesis of Pyrrole Derivatives in Aqueous Media
Further Information
Publication History
Received: 16 April 2013
Accepted after revision: 29 May 2013
Publication Date:
24 July 2013 (online)
Abstract
An improved catalyst-free, three-component reaction of ammonium acetate, 1,3-dicarbonyl compounds, and aromatic α-hydroxycarbonyl compounds has been carried out in water–ethanol (50:50) under reflux conditions. The improvement of yield in this aqueous medium is attributed to a combination of increased association of the reactants by hydrophobic interactions and precipitation of the product during the reaction. This operationally simple procedure is less laborious and provides a better scope and chemoselectivity than previously reported procedures.
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References and Notes
- 1 Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
- 2 Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
- 3 Minakata S, Komats M. Chem. Rev. 2009; 109: 711
- 4 Li CJ. Chem. Rev. 2005; 105: 3095
- 5a Heijden GV. D, Ruijter E, Orru RV. A. Synlett 2013; 24: 666
- 5b Yamamoto H, Sasaki I, Mitsutake M, Karasudani A, Imagawa H. Synlett 2011; 2815
- 6a Yadav JS, Subba Reddy BV, Srinivasa Rao T, Narender R, Gupta MK. J. Mol. Catal. A: Chem. 2007; 278: 42
- 6b Roland UB, Zeitler K, Müller TJ. J. Org. Lett. 2001; 3: 3297
- 6c Yoshida M, Al-Amin M, Shishido K. Synthesis 2009; 2454
- 7a Attanasi OA, Favi G, Mantellini F, Moscatelli G, Santeusanio S. J. Org. Chem. 2011; 76: 2860
- 7b Lin M, Hao L, Ma R.-d, Zhan Z.-p. Synlett 2010; 2345
- 8 Bharadwaj AR, Scheidt KA. Org. Lett. 2004; 6: 2465
- 9 Cox M, Lehninger AL, Nelson DR. Lehninger Principles of Biochemistry . Worth Publishers; New York: 2000
- 10a Bellina F, Rossi R. Tetrahedron 2006; 62: 7213
- 10b Yasui E, Wada M, Takamura N. Tetrahedron Lett. 2009; 50: 4762
- 10c Ghabraie E, Balalaie S, Bararjanian M, Bijanzade HR, Rominger F. Tetrahedron 2011; 67: 5415
- 11 Estévez V, Villacampa M, Menéndez JC. Chem. Soc. Rev. 2010; 39: 4402
- 12 Paradowski M, Lane CA. L. Synlett 2011; 1543
- 13 Sharland MC, Singkhonrat J, NajeebUllah M, Hayes SJ, Knight DW, Dunford DG. Tetrahedron Lett. 2011; 52: 2320
- 14a Tamaddon F, Farahi M, Karami B. J. Mol. Catal. A: Chem. 2012; 356: 85
- 14b Tamaddon F, Farahi M. Synlett 2012; 23: 1379
- 15 Sukhendu M, Srijit B, Umasish J. J. Org. Chem. 2010; 75: 1674
- 16a Anary-Abbasinejad M, Charkhati K, Anary-Ardakani H. Synlett 2009; 1115
- 16b Bhunia N, Das B. Synthesis 2013; 45: 1045
- 16c Das B, Reddy GC, Balasubramanyam P, Veeranjaneyulu B. Synthesis 2010; 1625
- 17 Adib M, Mahdavi M, Alizadeh Noghania M, Mirzaei P. Tetrahedron Lett. 2007; 48: 7263
- 18 Nagarapu L, Mallepalli R, Yeramanchi L, Bantu R. Tetrahedron Lett. 2011; 52: 3401
- 19a Tamaddon F, Razmi Z, Jafari AA. Tetrahedron Lett. 2010; 51: 1187
- 19b Tamaddon F, Bistgani JM. Synlett 2011; 2947
- 20 Jafari AA, Amini S, Tamaddon F. J. Appl. Polym. Sci. 2011; 125: 1339
- 21 Jafari AA, Moradgholi F, Tamaddon F. J. Org. Chem. 2009; 1249
- 22 Tamaddon F, Tayefi M, Hosseini E, Zare E. J. Mol. Catal. A: Chem. 2013; 366: 36
- 23 Nishi N, Koga K, Ohshima Ch, Yamamoto K, Nagashima U, Nagami K. J. Am. Chem. Soc. 1988; 110: 5246
- 24 General Procedure for the Synthesis of Substituted Pyrroles To a mixture of benzoin derivative (2 mmol) and 1,3-dicarbonyl compound (2 mmol) in H2O–EtOH (2 mL, 50:50) was added NH4OAc (4 mmol), and the mixture was stirred under reflux for the requisite time. After completion of the reaction (TLC), ice was added, and the product was isolated by filtration.
- 25 Trost BM. Science 1991; 254: 1471