Abstract
The heterogeneous annulation between 2-aminopyridines and propiolaldehydes was achieved in CH2Cl2 at 25 °C in the presence of 3 mol% of MCM-41-immobilised phosphine gold(I) complex (MCM-41-PPh3-AuCl) and AgSbF6 under air, yielding a variety of 3-acylimidazo[1,2-a] pyridines in good yields. This heterogeneous gold(I) catalyst can be easily prepared by a simple procedure, recovered by filtration of the reaction solution and recycled up to seven times without significant loss of activity.
References
1.
Marson C.M.
, Chem. Soc. Rev. , 2011 , 40 , 5514 .
2.
Trapani G.
,
Franco M.
,
Latrofa A.
,
Ricciardi L.
,
Carotti A.
,
Serra M.
,
Sanna E.
,
Biggio G.
, and
Liso G.
, J. Med. Chem. , 1999 , 42 , 3934 .
3.
Linton A.
,
Kang P.
,
Ornelas M.
,
Kephart S.
,
Hu Q.
,
Pairish M.
,
Jiang Y.
, and
Guo C.
, J. Med. Chem. , 2011 , 54 , 7705 .
4.
Bode M.L.
,
Gravestock D.
,
Moleele S.S.
,
van der Westhuyzen C.W.
,
Pelly S.C.
,
Steenkamp P.A.
,
Hoppe H.C.
,
Khan T.
, and
Nkabinde L.A.
, Bioorg. Med. Chem. , 2011 , 19 , 4227 .
5.
Bagdi A.K.
,
Santra S.
,
Monir K.
, and
Hajra A.
, Chem. Commun. , 2015 , 51 , 1555 .
6.
Bangade V.M.
,
Reddy B.C.
,
Thakur P.B.
,
Madhu Babu B.
, and
Meshram H.M.
, Tetrahedron Lett. , 2013 , 54 , 4767 .
7.
Jafarzadeh M.
,
Soleimani E.
,
Sepahvand H.
, and
Adnan R.
, RSC Adv. , 2015 , 5 , 42744 .
8.
Trapani G.
,
Franco M.
,
Ricciardi L.
,
Latrofa A.
,
Genchi G.
,
Sanna E.
,
Tuveri F.
,
Cagetti E.
,
Biggio G.
, and
Liso G.
, J. Med. Chem. , 1997 , 40 , 3109 .
9.
Kaswan P.
,
Pericherla K.
,
Saini H.K.
, and
Kumar A.
, RSC Adv. , 2015 , 5 , 3670 .
10.
Chernyak N.
, and
Gevorgyan V.
, Angew. Chem., Int. Ed. , 2010 , 49 , 2743 .
11.
DiMauro E.F.
, and
Kennedy J.M.
, J. Org. Chem. , 2007 , 72 , 1013 .
12.
Fu H.Y.
,
Chen L.
, and
Doucet H.
, J. Org. Chem. , 2012 , 77 , 4473 .
13.
Cao H.
,
Zhan H.
,
Lin Y.
,
Lin X.
,
Du Z.
, and
Jiang H.
, Org. Lett. , 2012 , 14 , 1688 .
14.
Yan R.-L.
,
Yan H.
,
Ma C.
,
Ren Z.-Y.
,
Gao X.-A.
,
Huang G.-S.
, and
Liang Y.-M.
, J. Org. Chem. , 2012 , 77 , 2024 .
15.
Bagdi A.K.
,
Rahman M.
,
Santra S.
,
Majee A.
, and
Hajra A.
, Adv. Synth. Catal. , 2013 , 355 , 1741 .
16.
Allahabadi E.
,
Ebrahimi S.
,
Soheilizad M.
,
Khoshneviszadeh M.
, and
Mahdavi M.
, Tetrahedron Lett. , 2017 , 58 , 121 .
17.
Chandra D.M.
,
Nageswara S.R.
, and
Adimurthy S.
, J. Org. Chem. , 2013 , 78 , 266 .
18.
He C.
,
Hao J.
,
Xu H.
,
Mo Y.P.
,
Liu H.
,
Han J.
, and
Lei A.
, Chem. Commun. , 2012 , 48 , 11073 .
19.
Santra S.
,
Bagdi A.K.
,
Majee A.
, and
Hajra A.
, Adv. Synth. Catal. , 2013 , 355 , 1065 .
20.
Cao H.
,
Liu X.
,
Liao J.
,
Huang J.
,
Qiu H.
,
Chen Q.
, and
Chen Y.
, J. Org. Chem. , 2014 , 79 , 11209 .
21.
Dorel R.
, and
Echavarren A.M.
, Chem. Rev. , 2015 , 115 , 9028 .
22.
Pennell M.N.
,
Foster R.W.
,
Turner P.G.
,
Halles H.C.
,
Tame C.J.
, and
Sheppard T.D.
, Chem. Commun. , 2014 , 50 , 1302 .
23.
Ueda H.
,
Yamaguchi M.
,
Kameya H.
,
Sugimoto K.
, and
Tokuyama H.
, Org. Lett. , 2014 , 16 , 4948 .
24.
Matuda Y.
,
Naoe S.
,
Oishi S.
,
Fujii N.
, and
Ohno H.
, Chem.-Eur. J. , 2015 , 21 , 1463 .
25.
He W.
,
Li C.
, and
Zhang L.
, J. Am. Chem. Soc. , 2011 , 133 , 8482 .
26.
Zhang Q.
,
Cheng M.
,
Hu X.
,
Li B.-G.
, and
Ji J.-X.
, J. Am. Chem. Soc. , 2010 , 132 , 7256 .
27.
Zhan H.
,
Zhao L.
,
Liao J.
,
Li N.
,
Chen Q.
,
Qiu S.
, and
Cao H.
, Adv. Synth. Catal. , 2015 , 357 , 46 .
28.
Cole-Hamilton D.J.
, Science , 2003 , 299 , 1702 .
29.
Phan N.T.S.
,
Sluys M.V.D.
, and
Jones C.W.
, Adv. Synth. Catal. , 2006 , 348 , 609 .
30.
Martin-Aranda R.M.
, and
Cejka J.
, Top. Catal. , 2010 , 53 , 141 .
31.
Villaverde G.
,
Corma A.
,
Iglesias M.
, and
Sanchez F.
, ACS Catal. , 2012 , 2 , 399 .
32.
Yang W.
,
Zhang R.
,
Yi F.
, and
Cai M.
, J. Org. Chem. , 2017 , 82 , 5204 .
33.
Zhao H.
,
He W.
,
Wei L.
, and
Cai M.
, Catal. Sci. Technol. , 2016 , 6 , 1488 .
34.
Nie Q.
,
Yi F.
,
Huang B.
, and
Cai M.
, Adv. Synth. Catal. , 2017 , 359 , 3968 .
