Abstract
An efficient method for the “one-pot” preparation of aryl Schiff bases is reported. In the presence of a selenium catalyst, the aryl Schiff bases have been prepared by a one-stage condensation of nitroarenes and aryl aldehydes using carbon monoxide as reducing agent at atmospheric pressure. The reductive condensation occurs with high selectivity regardless of the substituent groups on the aromatic ring without affecting other reducible functional groups.
References
1.
Ajamian A.
, and
Gleason J.L.
, Angew Chem. Int. Ed. , 2004 , 43 , 3754 .
2.
Xu Z.R.
, and
Lu X.Y.
, J. Org. Chem. , 1998 , 63 , 5031 .
3.
Hadjipavlou-Litina D.J.
, and
Geronikaki A.A.
, Drug Des. Discov. , 1996 , 15 , 199 .
4.
Doyle M.P.
,
Hu W.H.
, and
Timmons D.J.
, Org. Lett. , 2001 , 3 , 3741 .
5.
Higuchi M.
, and
Yamamoto K.
, Org. Lett. , 1999 , 1 , 1881 .
6.
Vicini P.
,
Geronikaki A.
,
Incerti M.
,
Busonera B.
,
Poni G.
,
Cabras C.A.
, and
Colla P.L.
, Bioorg. Med. Chem. , 2003 , 11 , 4785 .
7.
da Silva C.M.
,
da Silva D.L.
,
Modolo L.V.
,
Alves R.B.
,
de Resende M.A.
,
Martins C.V.B.
, and
de Fátima Â.
, J. Adv. Res. , 2011 , 2 , 1 .
8.
Schiff H.
, Ann. Chem. , 1867 , 140 , 93 .
9.
Macho V.
,
Kralik M.
,
Hudec J.
, and
Cingelova J.
, J. Mol. Catal. A: Chem. , 2004 , 209 , 69 .
10.
Zhang Y.
,
Ma K.
,
Li H.
,
He J.
,
Sun X.
,
Li R.
, and
Ma J.
, Catal. Lett. , 2009 , 128 , 465 .
11.
Tian F.S.
,
Yu Z.K.
, and
Lu S.W.
, J. Org. Chem. , 2004 , 69 , 4520 .
12.
Liu X.Z.
,
Lu S.W.
, J. Mol. Catal. A: Chem. , 2009 , 300 , 36 .
13.
Liu X.Z.
,
Lu S.W.
, Chem. Lett. , 2003 , 32 , 1142 .
14.
Miyata T.
,
Kondo K.
,
Murai S.
,
Hirashima T.
, and
Sonoda N.
, Angew. Chem., Int. Ed. Engl. , 1980 , 19 , 1008 .
15.
Nakamuka M.
,
Komastu K.
,
Gondo Y.
,
Ohta K.
, and
Veda Y.
, Chem. Pharm. Bull. , 1967 , 15 , 585 .
16.
Kaur M.B.
,
Sharma J.R.
, and
Marrao M.R.
, J. Indian Chem. Soc. , 2005 , 82 , 917 .
17.
Fannin K.
, J. Heterocycl. Chem. , 1967 , 4 , 301 .
18.
Sobanov A.A.
,
Zolotukhhia A.V.
,
Galkina I.V.
,
Galkin V.I.
, and
Cherkn Sov R.A.
, Russ. J. Gen. Chem. , 2006 , 76 , 421 .
