Abstract
A new approach for the synthesis of N–H ketoaziridines is described. 1-aminopyridinium iodide as a NH transferring agent provides a straightforward access to the 2-aroyl-3-arylaziridines from the corresponding 1,3-diarylprop-2-en-1-one. A possible general mechanism involving the N–N ylide is proposed.
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G.S. Singh, M. D’hooghe, N. De Kimpe, Chem. Rev. 107, 2080–2135 (2007)
X.E. Hu, Tetrahedron 60, 2701–2743 (2004)
S. Stankovic, M. D’hooghe, S. Catak, H. Eum, M. Waroquier, V. Waroquier, V.V. Speybroeck, N. De Kimpe, H.-J. Ha, Chem. Soc. Rev. 41, 643–665 (2012)
H. Stamm, J. Prakt. Chem. 341, 319–331 (1999)
H.A. Samimi, M. Mamaghani, K. Tabatabeian, J. Heterocycl. Chem. 45, 1765–1770 (2008)
F.G. Weber, H. Liepert, Z. Chem. 25, 175–176 (1985)
V.D. Orlov, F.G. Yaremenko, V.F. Lavrushin, Khim. Geterotsikl. Soedin. 1489–1491 (1980)
N.H. Cromwell, R.D. Babson, C.E. Harris, J. Am. Chem. Soc. 65, 312–315 (1943)
N.O. Mahmoodi, M.A. Zanjanchi, H. Kiyani, J. Chem. Res., Synop. 6, 438–440 (2004)
A.L. Tokes, G. Litkei, G. Janzso, Synth. Commun. 20, 1905–1913 (1990)
A.H. Blatt, J. Am. Chem. Soc. 61, 3494–3499 (1939)
I. Coldham, A.J. Collis, R.J. Mould, R.E. Rathmell, J. Chem. Soc. Perkin Trans. 1(21), 2739–2745 (1995)
I. Coldham, A.J. Collis, R.J. Mould, R.E. Rathmell, Tetrahedron Lett. 36, 3557–3560 (1995)
X.L. Jin, H. Sugihara, K. Daikai, H. Tateishi, Y.Z. Jin, H. Furuno, J. Inanaga, Tetrahedron 58, 8321–8329 (2002)
J. Xu, L. Ma, P. Jiao, Chem. Commun. 14, 1616–1617 (2004)
L. Ma, P. Jiao, Q. Zhang, D.-M. Du, J. Xu, Tetrahedron Asymmetry 18, 878–884 (2007)
E. Schmitz, K. Joehnisch, Khim. Geterotsikl. Soedin., 1629–1638 (1974)
K. Hori, H. Sugihara, Y.N. Ito, T. Katsuki, Tetrahedron Lett. 40, 5207–5210 (1999)
G. Chen, M. Sasaki, A.K. Yudin, Tetrahedron Lett. 47, 255–259 (2006)
E.J. Corey, M. Chaykovaky, J. Am. Chem. Soc. 87, 1353–1364 (1965)
C.R. Johnson, E.R. Janiga, J. Am. Chem. Soc. 95, 7692–7700 (1973)
S. Wers, A.V. Eremeev, D.A. Tikhomirov, E. Liepins, Khim Geterotsikl. Soedin., 426–429 (1975)
T. Schirmeister, Liebigs Ann. Recueill, 1895–1899 (1997)
R.N.T. Yoshimuram, S. Hisu, T. Akamaka, S. Oajz, Tetrahedron 36, 73–80 (1980)
A. Armstrong, D.R. Carbery, S.G. Lamont, A.R. Pape, R. Wincewicz, Synlett 2504–2506 (2006)
I. Ikeda, Y. Machii, M. Okahara, Synthesis 650–651 (1980)
J. Xu, P. J. Jiao, Chem. Soc., Perkin Trans. 1, 1491–1494 (2002)
A. Armstrong, C.A. Baxter, S.G. Lamont, A.R. Pape, R. Wincewicz, Org. Lett. 9, 351–353 (2007)
Y.-M. Shen, M.-X. Zhao, J. Xu, Y. Shi, Angew. Chem. Int. Ed. 45, 8005–8008 (2006)
H.A. Samimi, Z. Shams, J. Iran. Chem. Soc. 11, 979–984 (2014)
H.A. Samimi, S. Mohammadi, Synlett 24, 223–225 (2013)
H.A. Samimi, S. Mohammadi, J. Iran. Chem. Soc. 11, 69–73 (2014)
H.A. Samimi, B.M. Yamin, Z. Hiedari, L. Narimani, J. Heterocycl. Chem. in press DOI: 10.1002/jhet.2198
H.A. Samimi, B.M. Yamin, J. Chem. Res. 38, 358–361 (2014)
H.A. Samimi, H. Kiyani, Z. Shams, J. Chem. Res. 37, 282–284 (2013)
H.A. Samimi, B.M. Yamin, F. Saberi, Synthesis 47, 129–133 (2015)
H.A. Samimi, B.M. Yamin, M. Soltani, J. Iran. Chem. Soc. 11, 1467–1472 (2014)
R. Gösl, A. Meuwsen, Org. Synth. Coll. Vol. 5, 43–45 (1977)
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We are thankful to Research Council of Shahrekord University for supporting this work.
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Samimi, H.A., Momeni, A.R. Aminopyridinium iodide as a NH transferring agent for the synthesis of 2-aroyl-3-aryl aziridines. J IRAN CHEM SOC 12, 2221–2225 (2015). https://doi.org/10.1007/s13738-015-0700-2
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DOI: https://doi.org/10.1007/s13738-015-0700-2