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Facile Synthesis of Polysubstituted Cyclopropanes Using a-Tosyloxyketones
Corresponding Author(s) : Sonia Nain
Asian Journal of Chemistry,
Vol. 30 No. 3 (2018): Vol 30 Issue 3
Abstract
A facile synthesis of polysubstituted cyclopropanes (5) by the treatment of pyridinium ylides, generated in situ from pyridinium toslyates (2), with arylidenemalonitrile (4) is presented. Pyridinium toslyates (2) were obtained by reacting a-tosyloxyketones (1) with pyridine in benzene under reflux.
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- L.A. Wessjohann, W. Brandt and T. Thiemann, Chem. Rev., 103, 1625 (2003); https://doi.org/10.1021/cr0100188.
- H.U. Reissig and R. Zimmer, Chem. Rev., 103, 1151 (2003); https://doi.org/10.1021/cr010016n.
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- R. Faust, Angew. Chem. Int. Ed., 40, 2251 (2001); https://doi.org/10.1002/1521-3773(20010618)40:12<2251::AID-ANIE 2251>3.0.CO;2-R.
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References
L.A. Wessjohann, W. Brandt and T. Thiemann, Chem. Rev., 103, 1625 (2003); https://doi.org/10.1021/cr0100188.
H.U. Reissig and R. Zimmer, Chem. Rev., 103, 1151 (2003); https://doi.org/10.1021/cr010016n.
B.M. Trost, J.L. Gunzner, O. Dirat and Y.H. Rhee, J. Am. Chem. Soc., 124, 10396 (2002); https://doi.org/10.1021/ja0205232.
R. Faust, Angew. Chem. Int. Ed., 40, 2251 (2001); https://doi.org/10.1002/1521-3773(20010618)40:12<2251::AID-ANIE 2251>3.0.CO;2-R.
A. de Meijere, Chem. Rev., 103, 931 (2003); https://doi.org/10.1021/cr0100289.
H.N. Wong, M.Y. Hon, C.W. Tse, Y.C. Yip, J. Tanko and T. Hudlicky, Chem. Rev., 89, 165 (1989); https://doi.org/10.1021/cr00091a005.
H. Lebel, J.F. Marcoux, C. Molinaro and A.B. Charette, Chem. Rev., 103, 977 (2003); https://doi.org/10.1021/cr010007e.
O.G. Kulinkovich and A. de Meijere, Chem. Rev., 100, 2789 (2000); https://doi.org/10.1021/cr980046z.
J. Salaün, Cyclopropane Derivatives and their Diverse Biological Activities, In: Small Ring Compounds in Organic Synthesis, Springer Berlin Heidelberg, vol. VI, pp. 1-67 (2000).
B.M. Coleridge, C.S. Bello and A. Leitner, Tetrahedron Lett., 50, 4475 (2009); https://doi.org/10.1016/j.tetlet.2009.05.054.
(a) A.H. Hoveyda, D.A. Evans and G.C. Fu, Chem. Rev., 93, 1307 (1993); https://doi.org/10.1021/cr00020a002. (b) I. Nicolas, P. Le Maux and G. Simonneaux, Coord. Chem. Rev., 252, 727 (2008); https://doi.org/10.1016/j.ccr.2007.09.003.
H. Pellissier, Tetrahedron, 64, 7041 (2008); https://doi.org/10.1016/j.tet.2008.04.079.
(a) X.L. Sun and Y. Tang, Acc. Chem. Res., 41, 937 (2008); https://doi.org/10.1021/ar800108z. (b) C. Peppe, R.P. das Chagas and R.A. Burrow, J. Organomet. Chem., 693, 3441 (2008); https://doi.org/10.1016/j.jorganchem.2008.08.011. (c) Z.J. Ren, W.G. Cao, W.Y. Ding, Y. Wang and L.L. Wang, Synth. Commun., 34, 3785 (2004); https://doi.org/10.1081/SCC-200032500. (d) Z.J. Ren, W.G. Cao, J. Chen, Y. Wang and W.Y. Ding, Synth. Commun., 35, 3099 (2005); https://doi.org/10.1080/00397910500281176.
(a) J. Ackrell, J.M. Muchowski, E. Galeazzi and A. Guzman, J. Org. Chem., 51, 3374 (1986); https://doi.org/10.1021/jo00367a026. (b) C.D. Jones and T. Suarez, J. Org. Chem., 37, 3622 (1972); https://doi.org/10.1021/jo00796a012. (c) K. Senga, S. Nishigaki, M. Ichiba, J. Sato, M. Noguchi and F. Yoneda, Heterocycles, 9, 11 (1978); https://doi.org/10.3987/R-1978-01-0011. (d) N. De Kimpe, M. Boelens and J. Declercq, Tetrahedron, 49, 3411 (1993); https://doi.org/10.1016/S0040-4020(01)90168-1. (e) L.K.A. Rahman and R.M. Scrowston, J. Chem. Soc. Perkin Trans. I, 2973 (1983); https://doi.org/10.1039/p19830002973.
(a) O. Prakash, Aldrichim Acta, 28, 63 (1995); (b) O. Prakash and S.P. Singh, Aldrichim Acta, 27, 15 (1994); (c) O. Prakash and S. Goyal, Indian J. Heterocycl. Chem., 1, 103 (1991).
Q.F. Wang, X.K. Song, J. Chen and C.G. Yan, J. Comb. Chem., 11, 1007 (2009); https://doi.org/10.1021/cc900005v.
D. Aneja and O. Prakash, Heterolett., 2, 192 (2012).
O. Prakash, D. Wadhwa, K. Hussain and R. Kumar, Synth. Commun., 42, 2947 (2012); https://doi.org/10.1080/00397911.2011.570471.
R. Kumar, D. Wadhwa, K. Hussain and O. Prakash, Synth. Commun., 43, 1802 (2013); https://doi.org/10.1080/00397911.2012.671435.
Neena, S. Nain, D. Kumar and R. Kumar, Indian J. Heterocycl. Chem., 26, 107 (2016).