Abstract
A green and efficient synthesis of the trans-6-(4-chlorobenzoyl)-7-(aryl)-1,3-dimethyl-6,7-dihydrofuro[3,2-d]pyrimidine-2,4-diones has been achieved via a three-component, one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 1,3-dimethylbarbituric acid and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water under reflux conditions. This gives trans-6-(4-chlorobenzoyl)-7-(aryl)-1,3-dimethyl-6,7-dihydrofuro[3,2-d]pyrimidine-2,4-diones in excellent yield and in short reaction times.
Keywords
References
1.
Bhuiyan M.M.H.
,
Rahman K.M.M.
,
Hossain M.K.
,
Rahim M.A.
, and
Hossain M.I.
, Croat. Chem. Acta , 2005 , 78 , 633 .
2.
Gangiee A.
,
Zeng Y.
,
McGuire J.J.
, and
Kisliuk R.L.
, J. Med. Chem. , 2005 , 48 , 5329 .
3.
Gangjee A.
,
Zeng Y.
,
Ihnat M.
,
Warnke L.A.
,
Green D.W.
,
Kisliuk R.L.
, and
Lin F.-T.
, Bioorg. Med. Chem. , 2005 , 13 , 5475 .
4.
Gangjee A.
,
Zeng Y.
,
McGuire J.J.
,
Mehraein F.
, and
Kisliuk R.L.
, J. Med. Chem. , 2004 , 47 , 6893 .
5.
Dave C.G.
, and
Shah R.D.
, Molecules , 2002 , 7 , 554 .
6.
Gangiee A.
,
Zeng Y.
,
McGuire J.J.
, and
Kisliuk R.L.
, J. Med. Chem. , 2000 , 43 , 3125 .
7.
Janeba Z.
,
Balzarini J.
,
Andrei G.
,
Snoeck R.
,
De Clercq E.
, and
Robins M.J.
, J. Med. Chem. , 2005 , 48 , 4690 .
8.
Amblard F.
,
Aucagne V.
,
Guenot P.
,
Schinazi R.F.
, and
Agrofoglio L.A.
, Bioorg. Med. Chem. , 2005 , 13 , 1239 .
9.
Robins M.J.
,
Miranda K.
,
Rajwanshi V.K.
,
Peterson M.A.
,
Andrei G.
,
Snoeck R.
,
De Clercq E.
, and
Balzarini J.
, J. Med. Chem. , 2006 , 49 , 391 .
10.
Martin-Kohler A.
,
Widmer J.
,
Bold G.
,
Meyer T.
,
Séquin U.
, and
Traxler P.
, Helv. Chem. Acta , 2004 , 87 , 956 .
11.
Yamagata K.
,
Tomioka Y.
,
Yamazaki M.
, and
Noda K.
, Chem. Pharm. Bull. , 1983 , 31 , 401 .
12.
Yamagata K.
,
Tomioka Y.
, and
Yamazaki M.
, Chem. Pharm. Bull. , 1986 , 34 , 516 .
13.
Maruoka H.
,
Yamagata K.
, and
Yamazaki M.
, J. Heterocycl. Chem. , 2001 , 38 , 269 .
14.
Maruoka H.
,
Okabe F.
, and
Yamagata K.
, J. Heterocyclic Chem. , 2008 , 45 , 541 .
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.
Salari M.
,
Mosslemin M.H.
, and
Hassanabadi A.
, J. Chem. Res. , 2016 , 40 , 655 .
18.
Salari M.
,
Mosslemin M.H.
, and
Hassanabadi A.
, J. Chem. Res. (in press).
19.
Khan A.T.
,
Lal M.S.
, and
Basha R.
, Synthesis , 2013 , 45 , 406 .
20.
Anary-Abbasinejad M.
,
Charkhati K.
, and
Hassanabadi A.
, J. Chem. Res. , 2009 , 33 , 95 .
