Abstract
A straightforward, mild, efficient, one-pot method has been found for the synthesis of α-aminonitriles via three-component Strecker reaction using acetals or cyclic acetals, curious aromatic amines and trimethylsilyl cyanide (TMSCN) catalysed by hafnium tetrachloride at room temperature. It is with good to excellent yields under mild conditions. This developed approach has been successfully applied for the synthesis of a wild rang of α-aminonitriles with a variety of functional groups.
References
1.
Milroy L.G.
,
Zinzalla G.
,
Loiseau F.
,
Qian Z.
,
Prencipe G.
,
Pepper C.
,
Fegan C.
, and
Ley S.V.
, ChemMedChem , 2008 , 3 , 1922 .
2.
Dixon D.J.
,
Foster A.C.
,
Ley S.V.
, and
Reynolds D.J.
, J. Chem. Soc., Perkin Tran s. 1 , 1999 , 1635 .
3.
Chowdhury A.D.
, and
Lahiri G.K.
, Chem. Commun. , 2012 , 48 , 3448 .
4.
Mukaiyama T.
, and
Murakami M.
, Synthesis , 1987 , 1043 .
5.
Maity P.
,
Srinivas H.D.
, and
Watson M.P.
, J. Am. Chem. Soc. , 2011 , 133 , 17142 .
6.
Strecker A.L.
, Ann. Chim. , 1850 , 75 , 27 .
7.
Alejandro B.
,
Najera C.
, and
Sansano J.M.
, Synthesis , 2007 , 1230 .
8.
Nájera C.
, and
Sansano J.M.
, Chem. Rer. , 2007 , 107 , 4584 .
9.
Rajabi F.
,
Nourian S.
, and
Ghiassian S.
, Green Chem. , 2011 , 13 , 3282 .
10.
Vachal P.
, and
Jacobsen E.N.
, J. Am. Chem. Soc. , 2002 , 124 , 10012 .
11.
Paraskar S.
, and
Sudalai A.
, Tetrahedron Lett. , 2006 , 47 , 5759 .
12.
De S.K.
, and
Gibbs R.A.
, Tetrahedron Lett. , 2004 , 45 , 7407 .
13.
De S.K.
, J. Mol. Catal. A: Chem. , 2005 , 225 , 169 .
14.
Pasha M.A.
,
Nanjundaswamy H.M.
, and
Jayashankara V.P.
, Synth. Commun. , 2007 , 37 , 4371 .
15.
Shen Z.L.
,
Ji S.J.
, and
Loh T.P.
, Tetrahedron , 2008 , 64 , 8159 .
16.
Majhi A.
,
Kim S.S.
,
Kadam S.T.
, Tetrahedron , 2008 , 64 , 5509 .
17.
Chaturvedi D.
,
Chaturvedi A.K.
,
Mishra N.
, and
Mishra V.
, Tetrahedron Lett. , 2012 , 53 , 5398 .
18.
Swamy K.C.K.N.
,
Kumar N.B.
, and
Balaraman E.
, Chem. Rev. , 2009 , 109 , 2551 .
19.
Lee O.Y.
,
Law K.L.
,
Ho C.Y.
, and
Yang D.
, J. Org. Chem. , 2008 , 73 , 8829 .
20.
Dekamin M.G.
, and
Mokhtari Z.
Tetrahedron , 2012 , 68 , 922 .
21.
Khan N.H.
,
Agrawal S.
,
Kureshy R.I.
,
Abdi S.H.R.
,
Singh S.
,
Suresh E.
, and
Jasra R.V.
, Tetrahedron Lett. , 2008 , 49 , 640 .
22.
Lv D.X.
,
Bai Y.J.
, and
Yang T.
, Huaxue Tongbao , 2010 , 73 , 184 .
23.
Li Z.
,
Ma Y.H.
,
Xu J.
,
Shi J.H.
, and
Cai H.F.
, Tetrahedron Lett. , 2010 , 51 , 3922 .
24.
Wang H.S.
,
Zhao L.F.
, and
Du Z.M.
, Chin. J. Chem. , 2006 , 24 , 135 .
25.
Neelakantan L.
, and
Hartung W.H.
, J. Org. Chem. , 1959 , 24 , 1943 –1948 .
26.
Allen J.M.
, and
Lambert T.H.
, J. Am. Chem. Soc. , 2011 , 133 , 1260 –1262 .
27.
Kumar V.
,
Sharma U.
,
Verma P.K.
,
Kumar N.
, and
Singha B.
, Adv. Synth. Catal. , 2012 , 354 , 870 .
