Abstract
A one-pot, three-component condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl]isoquinolinium bromide with 4-hydroxycoumarin and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in refluxing water gave trans-2-(4-chlorobenzoyl)-3-(aryl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-ones in excellent yields and with short reaction times.
Keywords
References
1.
Wang X.
,
Bastow K. F.
,
Sun C. M.
,
Lin Y. L.
,
Yu H. J.
,
Don M. J.
,
Wu T. S.
,
Nakamura S.
, and
Lee K. H.
, J. Med. Chem. , 2004 , 47 , 5816 .
2.
Sardari S.
,
Mori Y.
,
Horita K.
,
Micetich R. G.
,
Nishibe S.
, and
Daneshtalab M.
, Bioorg. Med. Chem. , 1999 , 7 , 1933 .
3.
Al-Sehemi A.G.
, and
El-Gogary S. R.
, Chin. J. Chem. , 2012 , 30 , 316 .
4.
Campos-Toimil M.
,
Orallo F.
,
Santana L.
, and
Uriarte E.
, Bioorg. Med. Chem. Lett. , 2002 , 12 , 783 .
5.
Hishmat H.
,
abd el Rahman A. H.
,
Khalil Kh. M. A.
,
Moawad M. I.
, and
Atalla M. M.
, J. Pharm. Sci. , 1982 , 71 , 1046 .
6.
Marzano C.
,
Chilin A.
,
Baccichetti F.
,
Bettio F.
,
Guiotto A.
,
Miolo G.
, and
Bordin F.
, Eur. J. Med. Chem. , 2004 , 39 , 411 .
7.
Zareai Z.
,
Khoobi M.
,
Ramazani A.
,
Foroumadi A.
,
Souldozi A.
,
Slepokura K.
,
Lis T.
, and
Shafiee A.
, Tetrahedron , 2012 , 68 , 6721 .
8.
Altieri E.
,
Cordaro M.
,
Grassi G.
,
Risitano F.
, and
Scala A.
, Tetrahedron , 2010 , 66 , 9493 .
9.
Rajesh S.M.
,
Perumal S.
,
Menendez J. C.
,
Pandian S.
, and
Murugesan R.
, Tetrahedron , 2012 , 68 , 5631 .
10.
Wang Q.F.
,
Hou H.
,
Hui L.
, and
Yan C. G.
, J. Org. Chem. , 2009 , 74 , 7403 .
11.
Kumar A.
,
Srivastava S.
, and
Gupta G.
, Green Chem. , 2012 , 14 , 3269 .
12.
Tan X.C.
,
Zhao H. V.
,
Pan Y. M.
,
Wu N.
,
Wang H. S.
, and
Chen Z. F.
, RSC Adv. , 2015 , 5 , 4972 .
13.
Karanjule N.B.
, and
Samant S. D.
, Curr. Microwave Chem. , 2014 , 1 , 135 .
14.
Khan A.T.
,
Lal M. S.
, and
Basha R.
, Synthesis , 2013 , 45 , 406 .
15.
Li C.-J.
, and
Chan T.-H.
, Organic Reactions in Aqueous Media , Wiley , New York , 1997 .
16.
Jiménez-González C.
, and
Constable D. J. C.
, Green Chemistry and Engineering: A Practical Design Approach , Wiley , Hoboken , 2011 .
17.
Anary-Abbasinejad M.
,
Charkhati K.
, and
Hassanabadi A.
, J. Chem. Res. , 2009 , 2 , 95 .