Abstract
A greener synthesis of α-acyloxyamides was achieved by one-pot three component cascade Passerini reactions in a deep eutectic solvent (DES). Reactions proceeded rapidly and afforded the corresponding α-acyloxyamides by a variety of aldehydes, acids and isocyanides in excellent yields. The DES has the advantages of easy workup, high yield, and an environmentally benign and, moreover, shortened time as the greatest exclusivity of this system compared with previously reported methods.
Graphical Abstract
Passerini three-component cascade reaction in a deep eutectic solvent: an environmentally benign and rapid system for the synthesis of α-acyloxyamides.
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D. Reinhardt, F. Ilgen, D. Kralisch, B. König, G. Kreisel, Green Chem. 10, 1170 (2008)
A.P. Abbott, D. Boothby, G. Capper, D.L. Davies, R.K. Rasheed, J. Am. Chem. Soc. 126, 9142 (2004)
A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Chem. Commun. 70 (2003)
A.P. Abbott, R.C. Harris, K.S. Ryder, C. D’Agostino, L.F. Gladden, M.D. Mantle, Green Chem. 13, 82 (2011)
I. Mamajanov, A.E. Engelhart, H.D. Bean, N.V. Hud, Angew. Chem. Int. Ed. 49, 6310 (2010)
F. Pena-Pereira, J. Namieśnik, ChemSusChem 7, 1784 (2014)
F. del Monte, D. Carriazo, M.C. Serrano, M.C. Gutiérrez, M.L. Ferrer, ChemSusChem 7, 999 (2014)
M. Francisco, A. van den Bruinhorst, M.C. Kroon, Green Chem. 14, 2153 (2012)
D.V. Wagle, H. Zhao, G.A. Baker, Acc. Chem. Res. 47, 2299 (2014)
A. Rajawat, S. Khandelwal, M. Kumar, RSC Adv. 4, 5105 (2014)
P. Wang, F.-P. Ma, Z.-H. Zhang, J. Mol. Liq. 198, 259 (2014)
J. Lu, X.T. Li, E.Q. Ma, L.P. Mo, Z.H. Zhang, ChemCatChem 6, 2854 (2014)
A.A. Assanosi, M.M. Farah, J. Wood, B. Al-Duri, RSC Adv. 4, 39359 (2014)
N. Azizi, M. Mariami, M. Edrisi, Dyes Pigm. 100, 215 (2014)
H.-C. Hu, Y.-H. Liu, B.-L. Li, Z.-S. Cui, Z.-H. Zhang, RSC Adv. 5, 7720 (2015)
S. Handy, N.M. Westbrook, Tetrahedron Lett. 55, 4969 (2014)
I. Hawkins, S.T. Handy, Tetrahedron 69, 9200 (2013)
M. Bakavoli, H. Eshghi, M. Rahimizadeh, M.R. Housaindokht, A. Mohammadi, H. Monhemi, Res. Chem. Intermed. 41, 3497 (2013)
E.L. Smith, A.P. Abbott, K.S. Ryder, Chem. Rev. 114, 11060 (2014)
B.B. Toure, D.G. Hall, Chem. Rev. 109, 4439 (2009)
J.D. Sunderhaus, S.F. Martin, Chem. Eur. J. 15, 1300 (2009)
V. Estévez, M. Villacampa, J.C. Menéndez, Chem. Soc. Rev. 43, 4633 (2014)
A. Domling, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)
B. Ganem, Acc. Chem. Res. 42, 463 (2009)
O. Kreye, T. Tóth, M.A. Meier, J. Am. Chem. Soc. 133, 1790 (2011)
X.-X. Deng, L. Li, Z.-L. Li, A. Lv, F.-S. Du, Z.-C. Li, ACS Macro Lett. 1, 1300 (2012)
Y.-Z. Wang, X.-X. Deng, L. Li, Z.-L. Li, F.-S. Du, Z.-C. Li, Polym. Chem. 4, 444 (2013)
A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Mol. Divers. 15, 41 (2011)
A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)
A. Dömling, Chem. Rev. 106, 17 (2006)
R.H. Baker, D. Stanonis, J. Am. Chem. Soc. 73, 699 (1951)
H. Yanagita, E. Urano, K. Matsumoto, R. Ichikawa, Y. Takaesu, M. Ogata, T. Murakami, H. Wu, J. Chiba, J. Komano, Bioorg. Med. Chem. 19, 816 (2011)
J. Wu, W. Zhao, S. Cao, Eur. J. Org. Chem. 2012, 1380 (2012)
M. Mahyari, S. Shaabani, A. Shaabani, S. Weng Ng, Comb. Chem. High Throughput Screen. 16, 858 (2013)
P.R. Andreana, C.C. Liu, S.L. Schreiber, Org. Lett. 6, 4231 (2004)
M. Pirrung, J. Am. Chem. Soc. 126, 444 (2004)
C.K.Z. Andrade, S.C.S. Takada, P.A.Z. Suarez and M.B. Alves Synlett, 1539 (2006)
X. Fan, Y. Li, X. Zhang, G. Qu, J. Wang, Can. J. Chem. 84, 794 (2006)
D. Koszelewski, W. Szymanski, J. Krysiak, R. Ostaszewski, Synth. Commun. 38, 1120 (2008)
A.F.S. Barreto, O.E. Vercillo, C.K.Z. Andrade, J. Braz. Chem. Soc. 22, 462 (2011)
T. Bousquet, M. Jida, M. Soueidan, R. Deprez-Poulain, F. Agbossou-Niedercorn, L. Pelinski, Tetrahedron Lett. 53, 306 (2012)
A. Shaabani, R. Ghadari, A. Sarvary, A.H. Rezayan, J. Org. Chem. 74, 4372 (2009)
A. Shaabani, A. Sarvary, S. Ghasemi, A.H. Rezayan, R. Ghadari, S.W. Ng, Green Chem. 13, 582 (2011)
S. Shaabani, A. Shaabani, S.W. Ng, ACS Comb. Sci. 16, 176 (2014)
A. Shaabani, A.H. Rezayan, S. Keshipour, A. Sarvary, S.W. Ng, Org. Lett. 11, 3342 (2009)
A. Shaabani, E. Soleimani, A.H. Rezayan, A. Sarvary, H.R. Khavasi, Org. Lett. 10, 2581 (2008)
M.B. Teimouri, J. Chem. Res. 36, 432 (2012)
T. Kaicharla, S.R. Yetra, T. Roy, A.T. Biju, Green Chem. 15, 1608 (2013)
Acknowledgments
We gratefully acknowledge financial support from the Iran National Science Foundation (INSF), the Research Council of Shahid Beheshti University, and Catalyst Center of Excellence (CCE) at Shahid Beheshti University.
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Shaabani, A., Afshari, R. & Hooshmand, S.E. Passerini three-component cascade reactions in deep eutectic solvent: an environmentally benign and rapid system for the synthesis of α-acyloxyamides. Res Chem Intermed 42, 5607–5616 (2016). https://doi.org/10.1007/s11164-015-2390-x
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DOI: https://doi.org/10.1007/s11164-015-2390-x