Abstract
A one-potsynthesis of novel chromeno[3,2-f]quinoline derivatives has been achieved with good yields through Michael Initiated Ring Closure by employing a three-component condensation of an aromatic aldehyde, 5,5-dimethylcyclohexane-1,3-dione and 6-hydroxyquinoline in the presence of a catalytic amount of Et3N in ethanol under reflux conditions. The salient features of this protocol are a simple reaction procedure, good yields, avoidance of an aqueous work-up and simple purification by recrystallisation.
References
1.
Nasveld P.
, and
Kitchener S.
, Trans. R. Soc. Trop. Med. Hyg. , 2005 , 99 , 2 .
2.
Leatham P.A.
,
Bird H.A.
,
Wright V.
,
Seymour D.
, and
Gordon A.
, Eur. J. Rheumatol. Inflamm. , 1983 , 6 , 209 .
3.
Denny W.A.
,
Wilson W.R.
,
Ware D.C.
,
Atwell G.J.
,
Milbank J.B.
, and
Stevenson R.J.
, U.S. Patent: 7 064 117, issued 2006 .
4.
Mahamoud A.
,
Chevalier J.
,
Davin-Regli A.
,
Barbe J.
, and
Pages J.M.
, Curr. Drug Targets , 2006 , 7 , 843 .
5.
Muruganantham N.
,
Sivakumar R.
,
Anbalagan N.
,
Gunasekaran V.
, and
Leonard J.T.
, Biol. Pharm. Bull. , 2004 , 27 , 1683 .
6.
Maguire M.P.
,
Sheets K.R.
,
McVety K
,
Spada A.P.
, and
Zilberstein A.
, J. Med. Chem. , 1994 , 37 , 2129 .
7.
Kouznetsov V.V.
,
Mendez L.Y.
, and
Gomez C.M.
, Curr. Org. Chem. , 2005 , 9 , 141 .
8.
Al-Haiza M.A.
,
Mostafa M.S.
, and
El-Kad M.Y.
, Molecules , 2003 , 8 , 275 .
9.
Fylaktakidou K.C.
,
Hadipavlou-Litina D.J.
,
Litinas K.E.
, and
Nicolaides D.N.
, Curr. Pharm. Des. , 2004 , 10 , 3813 .
10.
Harvey R.G.
,
Cortex C.
,
Ananthanarayan T.P.
, and
Schmolka S.
, J. Org. Chem. , 1988 , 53 , 3936 .
11.
Kostova I.
,
Raleva S.
,
Genova P.
, and
Argirova R.
, Bioinorg, Chem. Appl. , 2006 , 68274 .
12.
Clark G.S.
, Perfum. Flavor. , 1995 , 20 , 23 .
13.
Brun M.P.
,
Bischoff L.
, and
Garbay C.
, Angew. Chem., Int. Ed. , 1995 , 43 , 3432 .
14.
Liu Y.
, and
Ding Y.
, Huaxue Yanjiu Yu Yingyong. , 1995 , 7 , 430 .
15.
Kym P.R.
,
Kort M.E.
,
Coghlan M.J.
,
Moore J.L.
,
Tang R.
, and
Ratajczyk J.D.
, J. Med. Chem. , 2003 , 46 , 1016 .
16.
Elmore S.W.
,
Pratt J.K.
,
Coghlan M.J.
,
Mao Y.
,
Green B.E.
,
Anderson D.
,
Stashko M.A.
,
Lin C.W.
,
Falls D.
,
Nakane M.
,
Miller L.
,
Tyree C.M.
,
Miner J.N.
, and
Lane B.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 1721 .
17.
Ku Y.Y.
,
Grieme T.
,
Raje P.
,
Sharma P.
,
Morton H.E.
,
Rozema M.
, and
King S.A.
, J. Org. Chem. , 2003 , 68 , 3238 .
18.
Zhi L.
,
Tegley C.M.
,
Pio B.
,
Edward J.P.
,
Motamedi M.
,
Jones T.D.
,
Marschke K.B.
,
Mais D.E.
,
Risek B.
, and
Schrader W.T.
, J. Med. Chem. , 1995 , 46 , 4104 .
19.
Khan A.T.
, and
Das D.K.
, Tetrahedron Lett. , 2012 , 53 , 2345 .
20.
Karade N.N.
,
Budheyar V.H.
,
Shine S.V.
, and
Jadhar W.N.
, Lett. Org. Chem. , 2007 , 4 , 16 .
