Abstract
A high-yielding synthesis of 1,2,4,5-tetrasubstituted imidazoles is described, involving the reaction of 1,2-dicarbonyl compounds, aryl aldehydes, amines and ammonium acetate in the presence of a catalytic amount of glutamic acid under thermal, solvent-free conditions. The salient features of this protocol are aerobic conditions, a non-hazardous green catalyst, short reaction times and mild reaction conditions.
Keywords
References
1.
Bora U.
,
Saikia A.R.
, and
Boruah C.
, Org. Lett. , 2003 , 5 , 435 .
2.
Weber L.
,
lllgen K.
, and
Almstetter N.
, Synlett , 1999 , 366 .
3.
Wolkenberg S.E.
,
Wisnoski D.D.
,
Leister W.H.
,
Wang Y.
,
Zhao Z.
, and
Lindsley C.W.
, Org, Lett. , 2004 , 6 , 1453 .
4.
Sisko J.
, J. Org. Chem. , 1998 , 63 , 4529 .
5.
Lambardino J.G.
, and
Wiesman E.H.
, J. Med. Chem. , 1974 , 17 , 1182 .
6.
Balalaei S.
, and
Arabanian A.
, Green Chem. , 2000 , 2 , 274 .
7.
Karimi A.R.
,
Alimohammadi Z.
,
Azizian J.
,
Mohammadi A.A.
, and
Mohmmadizadeh M.R.
, Catal. Commun. , 2006 , 7 , 728 .
8.
Kidwai M.
,
Mothsra P.
,
Bansal V.
,
Somvanshi R.K.
,
Ethayathulla A.S.
,
Dey S.
, and
Singh T.P.
, J. Mol. Catal. A: Chem. , 2007 , 265 , 177 .
9.
Nagarapu L.
,
Apuri S.
, and
Kantevari S.
, J. Mol. Catal. A: Chem. , 2007 , 266 , 104 .
10.
Javid A.
,
Heravi M.M.
,
Bamoharram F.F.
, and
Nikpour M.
, E-J. Chem. , 2011 , 8 , 547 .
11.
Akbari A.
, Tetrahedron Lett. , 2016 , 57 , 431 .
12.
Yugandar S.
,
Konda S.
,
Parameshwarappa G.
, and
Ila H.
, J. Org. Chem. , 2016 , 81 , 5606 .
13.
Sharma S.D.
,
Hazarika P.
, and
Konwar D.
, Tetrahedron Lett. , 2008 , 49 , 2216 .
14.
Kantevari S.
,
Vuppalapati S.V.N.
,
Biradar D.O.
, and
Nagarapu L.J.
, J. Mol. Catal. A: Chem. , 2007 , 266 , 109 .
15.
Sadeghi B.
,
Mirjalili B.B.F.
,
Bidaki S.
, and
Ghasemkhani M.
, J. Iran. Chem. Soc. , 2011 , 8 , 648 .
16.
Mekheimer R.A.
,
Hammeed A.M.A.
,
Mansour S.A.A.
, and
Sadek K.U.
, Chin. Chem. Lett. , 2009 , 20 , 812 .
17.
Kangani M.
,
Hazeri N.
,
Khandan-Barani K.
,
Maghsoodlou M.T.
,
Kheyrollahi M.
, and
Nezhadshahrokhabadi F.
, J. Iran. Chem. Soc. , 2015 , 12 , 47 .
18.
Khandan-Barani K.
,
Maghsoodlou M.T.
,
Habibi-Khorassani S.M.
,
Hazeri N.
, and
Sajadikhah S.S.
, Arkivoc , 2011 , xi , 22 .
19.
Khandan-Barani K.
,
Maghsoodlou M.T.
,
Hassanabadi A.
,
Hosseini-Tabatabaei M.R.
,
Saffari J.
, and
Kangani M.
, Res. Chem. Intermed. , 2015 , 41 , 3011 .
20.
Sharma R.K.
,
Sharma C.
, and
Prerna
, Indian J. Chem. , 2012 , 51B , 1489 .
21.
Nalage V.S.
,
Kalyankar1 M.B.
,
Patil V.S.
,
Bhosale S.V.
,
Deshmukh S.U.
, and
Pawar R.P.
, Open Catal. J. , 2010 , 3 , 58 .
22.
Manafi M.R.
,
Manafi P.
, and
Kalaee M.R.
, E-J. Chem , 2012 , 9 , 1773 .
23.
Teimouri A.
, and
Chermahini A.N.
, J. Mol. Catal. A: Chem. , 2011 , 346 , 39 .
24.
Ghaemy M.
,
Behmadi H.
, and
Alizadeh R.
, Chin. Chem. Lett. , 2009 , 20 , 961 .
25.
Sangshetti N.J.
,
Kokare N.D.
,
Kotharkar S.A.
, and
Shinde D.B.
, Chin. Chem. Lett. , 2008 , 19 , 762 .
26.
Samai S.
,
Chandra Nandi G.
,
Singh P.
, and
Singh M.S.
, Tetrahedron , 2009 , 65 , 10155 .