Abstract
The three-component reaction between 4-hydroxycoumarin, aromatic aldehydes and amides catalysed by p-toluenesulfonic acid in solvent-free conditions provided a simple and efficient one-pot route for the synthesis of 3-(α-amidobenzyl)-4-hydroxycoumarin derivatives in excellent yields.
Keywords
References
1.
Zhu J.
, and
Bienaymé H.
, Multicomponent reactions. Wiley-VCH , Weinheim , 2005 .
2.
Domling D.A.
, and
Ugi I.
, Angew. Chem, Int. Ed. , 2000 , 39 , 3168 .
3.
Weber L.
, Curr. Med. Chem. , 2002 , 9 , 1241 .
4.
O'Kennedy R.
, and
Thornes R.D.
, Coumarins: biology, applications and mode of action. John Wiley & Sons , Chichester , 1997 .
5.
Zabradnik M.
, The production and application of fluorescent brightening agents. John Wiley & Sons , New York , 1992 .
6.
Murray R.D.H.
,
Mendez J.
, and
Brown S.A.
, The natural coumarins: occurrence, chemistry and biochemistry. John Wiley & Sons , New York , 1982 .
7.
Raj G.
,
Kumar R.
, and
McKinney W.P.
, Am. J. Med. Sci. , 1994 , 307 , 128 .
8.
Hadler M.R.
, and
Shadbolt R.S.
, Nature , 1975 , 253 , 275 .
9.
Estevez-Braun A.
, and
Gonzalez A.G.
, Nat. Prod. Rep. 1997 , 14 , 465 .
10.
Clerici A.
, and
Porta O.
, Synthesis , 1993 , 99 .
11.
Misuno T.
,
Nishiguchi I.
,
Hirashima T.
,
Ogawa A.
,
Kambe N.
, and
Sonoda N.
, Synthesis , 1988 , 257 .
12.
Milne S.
,
Yan G.W.A.
,
Posey X.
,
Nicklaus I.J.
,
Graham M.C.
,
Wang L.
, and
Rice W.G.
, J. Med. Chem. 1996 , 39 , 2047 .
13.
Dittmer D.C.
,
Li Q.
, and
Avilov D.V.
, J. Org. Chem. 2005 , 70 , 4682 .
14.
Kalinin A.V.
, and
Snieckus V.
, Tetrahedron Lett. 1998 , 39 , 4999 .
15.
Kalinin A.V.
,
da Silva A.J.M.
,
Lopes C.C.
,
Lopes R.S.C.
, and
Snieckus V.
, Tetrahedron Lett. , 1998 , 39 , 4995 .
16.
Davis S.E.
,
Church A.C.
,
Tummons R.C.
, and
Beam D.C.F.
, J. Heterocycl. Chem. , 1997 , 34 , 1159 .
17.
Reddy C.R.
,
Srikanth B.
,
Rao N.N.
, and
Shin D.S.
, Tetrahedron , 2008 , 64 , 11666 .
18.
Anary-Abbasinejad M.
,
Anaraki-Ardakani H.
,
Saidipoor A.
, and
Shojaee M.
, J. Chem. Res. , 2007 , 537 .
19.
Anary-Abbasinejad M.
,
Anaraki-Ardakani H.
, and
Hassanabadi A.
, Synth. Commun. , 2008 , 38 , 3706 .
20.
Khodaei M.M.
,
Khosropour A.R.
, and
Moghanian H.
, Synlett , 2006 , 916 .
21.
Zhang P.
, and
Zhang Z.H.
, Monatsh. Chem. , 2009 , 140 , 199 .
22.
Das B.
,
Laxminarayana K.
,
Ravikanth B.
, and
Rama Rao B.
, J. Mol. Catal. A: Chem. , 2007 , 261 , 180 .
23.
Dorehgiraee A.
,
Khabazzadeh H.
, and
Saidi K.
Arkivoc , 2009 , 7 , 303 .