Abstract
In this study, efficient and mild synthesis of gem-dichloroaziridines from Schiff bases in the presence of nanocrystalline magnesium oxide/chloroform as a novel source of dichlorocarbene intermediate under thermal conditions have been described. The reaction is dramatically enhanced in the presence of nanocrystalline magnesium oxide, and any byproducts were detected during or after the reaction. The corresponding products have been obtained in excellent yields, high purity and short reaction times.
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D. Gulkova, O. Solcova, M. Zdrazil, Microporous Mesoporous Mater. 76, 137 (2004)
M.J. Climent, A. Corma, S. Iborra, M. Mifsud, J. Catal. 247, 223 (2007)
A. Ganguly, P. Trinh, K.V. Ramanujachary, T. Ahmad, A.M.A.K. Ganguli, J. Colloid Interface Sci 353, 137 (2011)
M.A. Faghihi-Sani, A. Yamaguchi, Ceram. Int. 28, 835 (2002)
R. Chaim, Z.J. Shen, M.J. Nygren, Mater. Res. 19, 2527 (2004)
D. Chen, E.H. Jordan, M. Gell, Scr Mater 59, 757 (2008)
H. Hattori, Chem. Rev. 95, 537 (1995)
B.M. Choudary, K.V.S. Ranganath, U. Pal, M.L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 127, 13167 (2005)
M.L. Kantam, U. Pal, B. Sreedhar, B.M. Choudary, Adv. Synth. Catal. 349, 1671 (2007)
B.M. Choudary, L.T. Chakrapani, K.V.R. Kumar, M.L. Kantum, Tetrahedron 62, 9571 (2006)
D. Jain, A. Rani, Am. Chem. Sci. J. 1, 37 (2011)
M. Reddy, S. Ashoka, G. Chandrappa, M. Pasha, Catal. Lett. 138, 82 (2010)
M. Seno, S. Shiraishi, Y. Suzuki, T. Asahara, Bull. Chem. Soc. Jpn. 51, 1413 (1978)
O.S. Petrov, V.I. Ognyanov, N.M. Mollov, Synthesis 637 (1987)
A.F. Khlebnikov, T.Yu. Nikiforova, M.S. Novikov, R.R. Kostikov, Synthesis 677 (1997)
M.K. Meilahn, L.L. Augenstein, J.L. McManaman, J. Org. Chem. 36, 3627 (1971)
Y. Ohshiro, H. Ohnishi, M. Komatsu, J. Jpn. Oil Chem. Soc. 36, 884 (1987)
E.K. Fields, J.M. Sandri, Chem. Ind. (London). 1216 (1959)
P.K. Kadaba, J.O. Edwards, J. Org. Chem. 25, 1431 (1960)
A.G. Cook, E.K. Fields, J. Org. Chem. 27, 3686 (1962)
M. Makosza, A. Kacprowicz, Rocz. Chem. 48, 2129 (1974)
A.F. Khlebnikov, M.S. Novikov, T.Yu. Nikiforova, R.R. Kostikov, Russ J. Org. Chem. 35, 91 (1999)
M.K. Meilahn, D.K. Olsen, W.J. Brittain, R.T. Anders, J. Org. Chem. 43, 1346 (1978)
J. Graefe, Zeitsschrift Fuer Chemie 14, 469 (1974)
G.S. Singh, M. D’hooghe, N. De Kimpe, Chem. Rev. 107, 2080 (2007)
E.Y. Shinkevich, K. Abbaspour Tehrani, A.F. Khlebnikov, M.S. Novikov, Tetrahedron 64, 7524 (2008)
M. Mihara, Y. Ishino, S. Minakata, M. Komatsu, J. Org. Chem. 70, 5320 (2005)
H. Naeimi, F. Salimi, Kh. Rabiei, J. Mol. Catal. A Chem 260, 100 (2006)
H. Naeimi, H. Sharghi, F. Salimi, Kh. Rabiei, Heteroatom Chem. 19, 43 (2008)
F. Meshkani, M. Rezaei, Powder Technol. 196, 85 (2009)
Acknowledgments
The authors are grateful to University of Kashan for supporting this work by Grant No. 159148/3.
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Naeimi, H., Rabiei, K., Rezaei, M. et al. Nanocrystalline magnesium oxide as a solid base catalyst promoted one pot synthesis of gem-dichloroaziridine derivatives under thermal conditions. J IRAN CHEM SOC 10, 161–167 (2013). https://doi.org/10.1007/s13738-012-0137-9
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DOI: https://doi.org/10.1007/s13738-012-0137-9