Abstract
An efficient one-pot synthesis of 2H-pyrroline derivatives by a simple reaction of β-enaminocarbonyls with arylglyoxals in water at room temperature is reported. The addition reaction between arylglyoxal derivatives and β-enaminocarbonyls in water afforded 3,4- dihydroxy-2H-pyrrolines after about 10 min stirring at room temperature. When the reaction was done in the presence of aromatic amines, the corresponding 4-amino-5-hydroxy-2H-pyrroline derivatives were obtained in good yields. All reactions were performed in water at room temperature and the products were isolated by simple filtration.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M.S. Butler, J. Nat. Prod. 67, 2141 (2004)
F. Bellina, R. Rossi, Tetrahedron. 62, 7213 (2006)
M.P. Green, J.C. Prodger, Hayes. J. Tetrahedron Lett. 43, 6609 (2002)
R. A. Batey, P. D. Simonic, D. Lin, R. P. Smyj, A. Lough, Chem. Commun. 651 (1999)
H. Ulbrich, B. Fiebich, B. Dannhardt, Eur. J. Med. Chem. 37, 953 (2002)
M.G.A. Shvekhgeimer, Khim. Geterotsiklicheskikh Soedin 583 (2003)
A.D. Melhado, M. Luparia, F.D. Toste, J. Am. Chem. Soc. 129, 12638 (2007)
E.V. Blyumin, H.J. Gallon, A.K. Yudin, Org. Lett. 9, 467 (2007)
X.F. Zhu, C.E. Henry, O. Kwon, Tetrahedron. 61, 6276 (2005)
P.Q. Huang, Synlett. 1133 (2006), S. Hourcade, A. Ferdenzi, P. Retailleau, S. Mons, C. Marazano, Eur. J. Org. Chem. 1302 (2005)
P. Garner, H.U. Kaniskan, J. Org. Chem. 70, 10868 (2005)
I. Yavari, M.J. Bayat, M. Sirouspour, S. Souri, Tetrahedron. 66, 7995 (2010)
S.R. Shengule, P. Karuso, Australian J. Chem. 64, 1617 (2011)
A.C. Spivey, R. Srikaran, C.M. Diaper, D. J. Turner. Org. Biomol. Chem. 1, 1638 (2003)
H.M. Hassneen, T.A. Abdallah, Molecules. 8, 333 (2003)
J.P. Michael, C.B. de Koning, D. Gravestock, G.D. Hosken, A.S. Howard, C.M. Jungmann, R.W.M. Krause, A.S. Parsons, S.C. Pelly, T.V. Stanbury, Pur. Appl. Chem. 71, 979 (1999)
J.E. Foster, J.M. Nicholson, R. Butcher, J.P. Stables, I.O. Edafiogho, A.M. Goodwin, M.C. Henson, C.A. Smith, K.R. Scott, Bioorg. Med. Chem. 7, 2415 (1999)
C. Cimarelli, G. Palmieri, E. Volpini, Synth. Commun. 31, 2943 (2001)
L.G. Beholz, P. Benovsky, D.L. Ward, N.S. Barta, J.R. Stille, J. Org. Chem. 62, 1033 (1997)
O. David, J. Blot, C. Bellec, M.C. Fargeau-Bellassoued, G. Haviari, J.P. Celerier, G. Lhommet, J.C. Gramain, D. Gradette, J. Org. Chem. 64, 3122 (1999)
H.M.C. Ferraz, F.L.C. Pereira, F.S. Leite, M.R.S. Nunes, Tetrahedron 55, 10915 (1999)
C.I. Herrerias, X. Yao, Z. Li, C. Li, Chem. Rev. 107, 2546 (2007)
B. Jiang, Q.Y. Li, H. Zhang, S.J. Tu, S. Pindi, G. Li, Org. Lett. 14, 700 (2012)
B. Jiang, M.S. Yi, F. Shi, S.J. Tu, S. Pindi, P. McDowell, G. Li, Chem. Commun. 48, 808 (2012)
B. Eftekhari-Sis, M. Zirak, A. Akbari, Chem. Rev. 113, 2958 (2013)
E. Caballero, P. Puebla, M. Domercq, M. Melanie, J.L. Lopez, A.S. Feliciano, Tetrahedron 50, 7849 (1994)
M. Anary-Abbasinejad, M. Talebizadeh, J. Iran. Chem. Soc. 11, 963 (2014)
M. Masoudi, M. Anary-Abbasinejad, J. Chem. Res. 39, 145 (2015)
M. Anary-Abbasinejad, A. Falahati, J. Iran. Chem. Soc. 12, 1415 (2015)
J.Y. Liu, Q.Y. Li, B. Jiang, S.J. Tu, RSC Advances. 3, 5056 (2013)
H.A. Riley, A.R. Gray, in Organic Syntheses (Wiley, New York, 1943)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Masoudi, M., Anary-Abbasinejad, M. & Mohammadi, M. An efficient one-pot synthesis of polyfunctionalized 2H-pyrroline derivatives by reaction of β-enaminocarbonyls, arylglyoxals and amines. J IRAN CHEM SOC 13, 315–321 (2016). https://doi.org/10.1007/s13738-015-0739-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-015-0739-0