Abstract
An efficient and novel method for the deamination of trans-1-alkyl (H or benzoyl)-2-aroyl aziridines in a completely stereo-controlled reaction in the presence of N-bromosuccinimide/cerium (IV) ammonium nitrate is described. In comparison with the previous reported work, this reaction reveals a substituent-reactivity relationship and important role for the substituent on C1 and C2 in determining whether deamination or oxidation reaction takes place.
References
1.
Yudin A.K.
, Ed. Aziridines and epoxides in organic synthesis. Wiley-VCH : Weinheim , 2006 .
2.
Singh G.S.
,
D'hooghe M.
, and
De Kimpe N.
, Chem. Rev. , 2007 , 107 , 2080 .
3.
Nielsen D.K.
,
Huang C.-Y.
, and
Doyle A.G.
, J. Am. Chem. Soc. , 2013 , 135 , 13605 .
4.
Ilardi E.A.
, and
Njardarson J.T.
, J. Org. Chem. , 2013 , 78 , 9533 .
5.
Lee K.
, and
Kim Y.H.
, Synth. Commun. , 1999 , 29 , 1241 .
6.
Krishnaiah M.D.
, and
Venkateswarlu K.
, Chem. Lett. , 2007 , 36 , 82 .
7.
Guo Z.
, and
Schultz A.Z.
, Tetrahedron Lett. , 2004 , 45 , 919 .
8.
Roehn U.
,
Becaud J.
,
Mu L.
,
Srinivasan A.
,
Stellfeld T.
,
Fitzner A.
,
Graham K.
,
Dinkelborg
,
Schubiger L.A.P.
, and
Ametamey S.M.
, J. Fluorine. Chem. , 2009 , 130 , 902 .
9.
Lee K.
, and
Kim Y.H.
, Synth. Commun. , 1999 , 29 , 1241 .
10.
Clark R.D.
, and
Helmkamp G.K.
, J. Org. Chem. , 1964 , 29 , 1316 .
11.
Fleming I.
,
Frackenpohl J.
, and
Ila H.
, J. Chem. Soc. Perkin Trans. 1 , 1998 , 229 –236 .
12.
Samimi H.A.
,
Shams Z.
, and
Momeni A.R.
, J. Iran. Chem. Soc. , 2012 , 9 , 705 .
13.
Samimi H.A.
, and
Mohammadi S.
, J. Iran. Chem. Soc. , 2014 , 11 , 69 .
14.
Samimi H.A.
, and
Shams Z.
, J. Iran. Chem. Soc. , 2014 , 11 , 979 .
15.
Samimi H.A.
,
Mamaghani M.
, and
Tabatabeian Kh.
, J. Heterocyclic Chem. , 2008 , 45 , 1765 .
16.
Mamaghani M.
,
Tabatabeian Kh.
, and
Samimi H.A.
, Z. Kristallogr. NCS , 2008 , 223 , 390 .
17.
Samimi H.A.
, and
Mohammadi S.
, Synlett , 2013 , 24 , 223 .
18.
Samimi H.A.
,
Kiyani H.
, and
Shams Z.
, J. Chem. Res. , 2013 , 37 , 282 .
19.
Samimi H.A.
,
Yamin B.M.
,
Hiedari Z.
, and
Narimani L.
, J. Heterocyclic Chem. , 2014 (in press).
20.
Samimi H.A.
, and
Yamin B.M.
, J. Chem. Res. , 2014 , 38 , 358 .
21.
Gabriel S.
, Chem. Ber. , 1888 , 21 , 1049 .
22.
Armstrong A.
,
Baxter C.A.
,
Lamont S.G.
,
Pape A.R.
, and
Wincewicz R.
, Org. Lett. , 2007 , 9 , 351 .
23.
Shen Y.-M.
,
Zhao M.-X.
,
Xu J.
, and
Shi Y.
, Angew. Chem. Int. Ed. , 2006 , 45 , 8005 .
24.
Lopez S.N.
,
Castelli M.V.
,
Zacchino S.A.
,
Dominguez J.N.
,
Lobo G.
,
Charris–Charris J.
,
Cortes J.C.G.
,
Ribas J.C.
,
Devia C.
,
Rodriguez A.M.
, and
Enriz R.D.
, Bioorg. Med. Chem. , 2001 , 9 , 1999 .
25.
Montes-Avila J.
,
Diaz-Camacho S.P.
,
Sicairos-Felix J.
,
Delgado-Vargas F.
, and
Rivero I.A.
, Bioorg. Med. Chem. , 2009 , 17 , 6780 .
26.
Surendra K.
,
Srilakshmi Krishnaveni N.
, and
Rama Rao K.
, Tetrahedron Lett. , 2005 , 46 , 4111 .
27.
Somi Reddy M.
,
Narender M.
, and
Rama Rao K.
Tetrahedron Lett. , 2005 , 46 , 1299 .