Abstract
Under mild microwave irradiation conditions a variety of symmetrical and unsymmetrical N,N′-disubstituted thioureas and ureas were prepared via the reaction of N-monosubstituted hydroxylamines with isocyanate and isothiocyanate derivatives over MgO under solvent-free conditions. This new method afforded satisfactory results with good yields, short reaction time, and simplicity in the experimental procedure.
Graphical abstract
Similar content being viewed by others
References
Tanaka K, Toda F (2000) Chem Rev 100:1025
Lu YJ, Sun N, Huang ZS, Gu LQ (2008) Chin Chem Lett 19:518
Zarei A, Hajipour AR, Khazdooz L (2010) Dyes Pigm 85:133
Castanheiro RAP, Pinto MMM, Cravo SMM, Pinto DCGA, Silva AMS, Kijjoa A (2009) Tetrahedron 65:3848
Rostamizadeh S, Ghaieni HR, Aryan R, Amani AM (2010) Tetrahedron 66:494
Schroeder DC (1955) Chem Rev 55:181
Esteves-Souza A, Echevarría A, Vencato J, Jimeno ML, Elguero J (2001) Tetrahedron 57:6147
Tobe Y, Sasaki S, Mizuno M, Hirose K, Naemura K (1998) J Org Chem 63:7481 (and references cited therein)
Becker A, Heizler W (1983) Helv Chim Acta 66:1011
Criton M, Le VM-H (2008) Bioorg Med Chem Lett 18:3607
Ludwig BJ, Dürsch F, Auerbach M, Tomeczek K, Berger FM (1967) J Med Chem 10:556
Luk’yanov OA, Gordeev PB (1999) Russian Chem Bull 48:2302
Grigat E, Pütter R, König C (1965) Chem Ber 98:144
Douglas GH, Diamond J, Studt WL, Mir GN, Alioto RL, Auyang K, Burns BJ, Cias J, Darkes PR, Dodson SA, O’Connor S, Santora NJ, Tsuei CT, Zalipsky JJ, Zimmerman HK (1978) Arzneimittelforschung 28:1435
Vogel AI (1954) A textbook of organic chemistry. Longmans, London, p 614
Ballini R, Bosica G, Fiorini D, Maggi R, Righi P, Sartori G, Sartorio R (2002) Tetrahedron Lett 43:8445
Aravindakshan PA, Bhramaramba A, Nair GV, Nambury CNV (1963) Indian J Chem 1:395
Blanco JLJ, Barría CS, Benito JM, Mellet CO, Fuentes J, Santoyo-Gonzáles F, Fernández JMG (1999) Synthesis 1907
Moutou J-L, Schmitt M, Collot V, Bourguignon J-J (1981) Tetrahedron 37:1781
Herr RJ, Kuhler JL, Meckler H, Opalka CJ (2000) Synthesis 1569 (and references cited therein)
Valizadeh H, Vaghefi S (2009) Synth Commun 39:1666
Valizadeh H, Heravi MM, Amiri M (2010) Mol Divers 14:575
Valizadeh H (2010) Heteroatom Chem 21:78
Valizadeh H, Shockravi A (2005) Tetrahedron Lett 46:3501
Valizadeh H, Mamaghani M, Badrian A (2005) Synth Commun 35:785
Valizadeh H, Fakhari A (2010) Molecules 15:2972
Valizadeh H, Gholipour H (2010) Synth Commun 40:1477
Ambati NB, Anand V, Hanumanthu P (1997) Synth Commun 27:1487
Snyder JK, Stock LM (1980) J Org Chem 45:886
Hofmann AW (1868) Chem Ber 1:27
Nair GV (1965) J Indian Chem Soc 42:359
Izdebski J, Pawlak D (1989) Synthesis 423
Zywucki B, Jadzyn J, Stockhausen M, Steffen A (1989) J Mol Struct 193:51
Acknowledgments
The partial financial assistance from the Research Vice Chancellor of Azarbaijan University of Tarbiat Moallem is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Valizadeh, H., Dinparast, L. Microwave-assisted synthesis of symmetrical and unsymmetrical N,N′-disubstituted thioureas and ureas over MgO in dry media. Monatsh Chem 143, 251–254 (2012). https://doi.org/10.1007/s00706-011-0583-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-011-0583-6