Abstract
The heterogeneous coupling reaction of oxime acetates with isothiocyanates was achieved at 110 °C in toluene in air in the presence of a bidentate nitrogen-functionalised MCM-41-immobilised copper(I) complex (MCM-41-2N-CuI) with Cs2CO3 as base to afford a variety of 2-aminothiazoles in good yields. The MCM-41-2N-CuI catalyst can be easily recovered by a simple filtration and reused at least eight times without significant loss of activity.
References
1.
Zhao M.
,
Yin J.
,
Huffman M.A.
, and
McNamara J.M.
, Tetrahedron , 2006 , 62 , 1110 .
2.
Baell J.B.
, and
Holloway G.A.
, J. Med. Chem. , 2010 , 53 , 2719 .
3.
Gallardo-Godoy A.
,
Gever J.
,
Fife K.L.
,
Silber B.M.
,
Prusiner S.B.
, and
Renslo A.R.
, J. Med. Chem. , 2011 , 54 , 1010 .
4.
Gupta R.R.
,
Kumar M.
, and
Gupta V.
, Heterocyclic chemistry. Springer Publishing Group , 2005 , Vol. II .
5.
Hantzsch A.
, and
Weber J.H.
, Ber. Dtsch. Chem. Ges. , 1887 , 20 , 3118 .
6.
Keamey P.C.
,
Fernandez M.
, and
Flygare J.A.
, J. Org. Chem. , 1998 , 63 , 196 .
7.
Potewar T.M.
,
Ingale S.A.
, and
Srinivasan K.V.
, Tetrahedron , 2008 , 64 , 5019 .
8.
Kabalka G.W.
, and
Mereddy A.R.
, Tetrahedron Lett. , 2006 , 47 , 5171 .
9.
Siddiqui H.L.
,
Iqbal A.
,
Ahmed S.
, and
Weaver G.
, Molecules , 2008 , 11 , 206 .
10.
Karade H.
,
Sathe M.
, and
Kaushik M.P.
, Catal. Commun. , 2007 , 8 , 741 .
11.
Potewar T.M.
,
Ingale S.A.
, and
Srinivasan K.V.
, Tetrahedron , 2007 , 63 , 11066 .
12.
Das B.
,
Reddy S.V.
, and
Ramu R.
, J. Mol. Catal. A: Chem. , 2006 , 252 , 235 .
13.
Narender M.
,
Reddy M.S.
,
Sridhar R.
,
Naggeswar K.
, and
Rao K.
, Tetrahedron Lett. , 2005 , 46 , 7779 .
14.
Yin G.
,
Ma J.
,
Shi H.
, and
Tao Q.
, Heterocycles , 2012 , 85 , 1941 .
15.
Zhao J.
,
Xu J.
,
Chen J.
,
He M.
, and
Wang X.
, Tetrahedron , 2015 , 71 , 539 .
16.
Ghodse S.M.
, and
Telvekar V.N.
, Tetrahedron Lett. , 2015 , 56 , 472 .
17.
Tang X.
,
Zhu Z.
,
Qi C.
,
Wu W.
, and
Jiang H.
, Org. Lett. , 2016 , 18 , 180 .
18.
Iwasawa Y.
, Tailored metal catalysis. Reidel D. Publishing Company , Dordrecht, Holland , 1986 .
19.
Benyahya S.
,
Monnier F.
,
Taillefer M.
,
Man M.W.C.
,
Bied C.
, and
Ouazzani F.
, Adv. Synth. Catal. , 2008 , 350 , 2205 .
20.
Benyahya S.
,
Monnier F.
,
Man M.W.C.
,
Bied C.
,
Ouazzani F.
, and
Taillefer M.
, Green Chem. , 2009 , 11 , 1121 .
21.
Kresge C.T.
,
Leonowicz M.E.
,
Roth W.J.
,
Vartuli J.C.
, and
Beck J.S.
, Nature , 1992 , 359 , 710 .
22.
Beck J.S.
,
Vartuli J.C.
,
Roth W.J.
,
Leonowicz M.E.
,
Kresge C.T.
,
Schmitt K.D.
,
Chu C.T.-W.
,
Olson D.H.
,
Sheppard E.W.
,
McCullen S.B.
,
Higgins J.B.
, and
Schlenker J.L.
, J. Am. Chem. Soc. , 1992 , 114 , 10834 .
23.
Martin-Aranda R.M.
, and
Cejka J.
, Top. Catal. , 2010 , 53 , 141 .
24.
Mehnert P.C.
,
Weaver D.W.
, and
Ying J.Y.
, J. Am. Chem. Soc. , 1998 , 120 , 12289 .
25.
Mukhopadhyay K.
,
Sarkar B.R.
, and
Chaudhari R.V.
, J. Am. Chem. Soc. , 2002 , 124 , 9692 .
26.
Cai M.
,
Zheng G.
, and
Ding G.
, Green Chem. , 2009 , 11 , 1687 .
27.
Hao W.
,
Liu H.
,
Yin L.
, and
Cai M.
, J. Org. Chem. , 2016 , 81 , 4244 .
28.
Shyu S.-G.
,
Cheng S.-W.
, and
Tzou D.-L.
, Chem. Commun. , 1999 , 2337 .
29.
Jia M.
,
Seifert A.
, and
Thiel W. R.
, Chem. Mater. , 2003 , 15 , 2174 .
30.
Corma A.
,
Gutierrez-Puebla E.
,
Iglesias M.
,
Monge A.
,
Perez-Ferreras S.
, and
Sanchez F.
, Adv. Synth. Catal. , 2006 , 348 , 1899 .
31.
Corma A.
,
Gonzalez-Arellano C.
,
Iglesias M.
, and
Sanchez F.
, Angew. Chem., Int. Ed. , 2007 , 46 , 7820 .
32.
Villaverde G.
,
Corma A.
,
Iglesias M.
, and
Sanchez F.
, ACS Catal. , 2012 , 2 , 399 .
33.
Xiao R.
,
Zhao H.
, and
Cai M.
, Tetrahedron , 2013 , 69 , 5444 .
34.
Zhao H.
,
He W.
,
Yao R.
, and
Cai M.
, Adv. Synth. Catal. , 2014 , 356 , 3092 .
35.
Zhao H.
,
He W.
,
Wei L.
, and
Cai M.
, Catal. Sci. Technol. , 2016 , 6 , 1488 .
36.
Lempers H.E.B.
, and
Sheldon R.A.
, J. Catal. , 1998 , 175 , 62 .
37.
Too P.C.
,
Wang Y.-F.
, and
Chiba S.
, Org. Lett. , 2010 , 12 , 5688 .
38.
Potewar T.M.
,
Ingale S.A.
, and
Srinivasan K.V.
, Tetrahedron , 2008 , 64 , 5019 .
39.
Kidwai M.
,
Chauhan R.
, and
Bhatnagar D.
, J. Sulfur Chem. , 2011 , 32 , 37 .
40.
Kidwai M.
,
Bhatnagar D.
,
Mothsra P.
,
Singh A.K.
, and
Dey S.
, J. Sulfur Chem. , 2009 , 30 , 29 .