Document Type : Original Research Article


Imam Hossein University, Tehran, Iran


A mild and efficient one-pot three-component and environmentally benign approach for the synthesis of a wide range of hydantoin annulated derivatives has been described. A multi-component reaction between a carbonyl compounds (ketone or aldehyde), potassium cyanide and ammonium carbonate (as cyanating agent and amine source, respectively leads to the formation of hydantoins. The proposed optimized reaction conditions ,i.e. solvent-free conditions under ambient temperature in the presence of low amount of ZnOnano-catalyst, were very efficient resulting in the formation of the desired products with good to excellent yields. Furthermore, the presented methodology is in accord with green chemistry principles.
Keywords: Bucherer-Bergs; hydantoin derivatives; multicomponent reactions (MCRs); green chemistry.

Graphical Abstract

Highly efficient and rapid synthesis of diverse hydantoin derivatives using nano-ordered ZnO catalyst under mechanochemical ball milling


Main Subjects

[1] A. Baeyer, Justus Liebigs Ann. Chem., 1861, 119, 126-128.
[2] D. Zhang, D. Ye, E. Feng, J. Wang, J. Shi, H. Jiang, H. Liu, The Journal of Organic Chemistry, 2010, 75, 3552-3557.
[3] Basappa, C.S. Ananda Kumar, S. Nanjunda Swamy, K. Sugahara and K. S. Rangappa, Bioorganic & Medicinal Chemistry, 2009, 17, 4928-4934.
[4] P.T. Todorov, E.D. Naydenova, Comptes Rendus Chimie, 2010, 13, 1424-1428.
[5] F. Goubet, G. Teutsch, Tetrahedron Letters, 1996, 37, 7727-7730.
[6] A. Mandal, R.S.G. Krishnan, S. Thennarasu, S. Panigrahi, A.B. Mandal, Colloids and Surfaces B: Biointerfaces 2010, 79, 136-141.
[7] A. Daugan, P. Grondin, C. Ruault, A.-C. Le Monnier de Gouville, H. Coste, J. Kirilovsky, F. Hyafil, R. Labaudinière, Journal of Medicinal Chemistry, 2003, 46, 4525-4532.
[8] A. Volonterio, C. Ramirez de Arellano, M. Zanda, The Journal of Organic Chemistry 2005, 70, 2161-2170.
[9] Y. Brouillette, V. Lisowski, J. Guillon, S. Massip, J. Martinez, Tetrahedron, 2007, 63, 7538-7544.
[10] A. Alizadeh, E. Sheikhi, Tetrahedron Letters, 2007, 48, 4887-4890.
[11] M. Sañudo, M. García-Valverde, S. Marcaccini, T. Torroba, Tetrahedron, 2012, 68, 2621-2629.
[12] M. Meusel and M. Gütschow, Organic Preparations and Procedures International, 2004, 36, 391-443.
[13] A. Dömling and I. Ugi, Angewandte Chemie International Edition, 2000, 39, 3168-3210.
[14] a) S. Brauch, S.S. van Berkel, B. Westermann, Chemical Society Reviews, 2013, 42, 4948-4962; b) R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chemistry, 2014, 16, 2958-2975.
[15] a) R.G. Murray, D.M. Whitehead, F. Le Strat, S.J. Conway, Organic & Biomolecular Chemistry, 2008, 6, 988-991; b) J. Safari, L. Javadian, Journal of Chemical Sciences, 2013, 125, 981-987.
[16] A. Stolle, T. Szuppa, S.E.S. Leonhardt, B. Ondruschka, Chemical Society Reviews, 2011, 40, 2317-2329.
[17] D. Sharma, J. Rajput, B. S. Kaith, M. Kaur, S. Sharma, Thin Solid Films, 2010, 519, 1224-1229.
[18] R. Massart, Magnetics, IEEE Transactions on, 1981, 17, 1247-1248.
[19] R. Ghahremanzadeh, M. Sayyafi, S. Ahadi, A. Bazgir, Journal of Combinatorial Chemistry, 2009, 11, 393-396.
[20] N. O. Mahmoodi, Z. Khodaee, Arkivoc, 2007, 3, 29-36.
[21] H.R. Henze, R.J. Speer, Journal of the American Chemical Society, 1942, 64, 522-523.
[22] J. Safari, L. Javadian, Comptes Rendus Chimie, 2013, 16, 1165-1171.
[23] J. Li, L. Li, T. Li, H. Li, J. Liu, Ultrasonics Sonochemistry, 1996, 3, S141-S143.