Abstract
4,6-Diarylpyrimidin-2(1H)-ones were effectively synthesised by utilising chlorotrimethylsilane (TMSCI) as an efficient promoter in the cyclisation condensation of arylketones, substituted benzaldehydes and urea by a one-pot, three-component reaction under air in DMF/CH3CN. The clean, mild reaction conditions, operational simplicity and high yields were attractive features of the reaction which enables a facile preparative procedure for building the pyrimidine ring.
References
1.
Yang J.
,
Dang Q.
,
Liu J.
,
Wei Z.
,
Wu J.
, and
Bai X.
, J. Comb. Chem. , 2005 , 7 , 474 .
2.
Dang Q.
, and
Gomez-Galeno J. E.
, J. Org. Chem. , 2002 , 67 , 8703 .
3.
Bork J.T.
,
Lee J.W.
, and
Chang Y.-T.
, QSAR Comb. Sci. , 2004 , 23 , 245 .
4.
Lagoja I.M.
, Chem. Biodiv. , 2005 , 2 , 1 .
5.
Otmar M.
,
Masojidkova M.
,
Votruba I.
, and
Holy A.
, Bioorg. Med. Chem. , 2004 , 12 , 3187 .
6.
Breault G.A.
,
Ellston R.P.A.
,
Green S.
,
James S.R.
,
Jewsbury P.J.
,
Midgley C.J.
,
Pauptit R.A.
,
Minshull C.A.
,
Tucker J.A.
, and
Pease J.E.
, Bioorg. Med. Chem. Lett. , 2003 , 13 , 2961 .
7.
Gong B.
,
Hong F.
,
Kohm C.
,
Jenkins S.
,
Tulinsky J.
,
Bhatt R.
,
de Vries P.
,
Singer J.W.
, and
Klein P.
, Med. Chem. Lett. , 2004 , 14 , 2303 .
8.
Provins L.
,
Christophe B.
,
Danhaive P.
,
Dulieu J.
,
Durieu V.
,
Gillard M.
,
Lebon F.
,
Quere S.L.
, and
van Keulen B.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 1834 .
9.
Zhang H.
,
Schinazi R.F.
, and
Chu C.K.
, Bioorg. Med. Chem. , 2006 , 14 , 8314 .
10.
Undheim K.
, and
Benneche T.
, Comprehensive heterocyclic chemistry II;
Katritzky A. R.
,
Rees C. W.
, and
Scriven E. V. F.
, eds, Pergamon Press , London , 1996 ; Vol. 6 , Chapter 2, p 93 .
11.
Brown D. J.
,
Evans R.F.
, and
Cowden W.B.
, The pyrimidines ,
Taylor E.C.
, and
Weissberger A.
, eds, John Wiley , New York , 1994 ; Vol. 52 , p 1 .
12.
Johar M.
,
Manning T.
,
Kunimoto D.Y.
, and
Kumar R.
, Bioorg. Med. Chem. , 2005 , 13 , 6663 .
13.
Azas N.
,
Rathelot P.
,
Djekou S.
,
Delmas F.
,
Gellis A.
,
Di Giorgio C.
,
Vanelle P.
, and
Timon-David P.
, Il Farmaco , 2003 , 58 , 1263 .
14.
Agarwal A.
,
Srivastava K.
,
Puri S.K.
, and
Chauhan P.M.S.
, Bioorg. Med. Chem. , 2005 , 13 , 4645 .
15.
Gompper R.
,
Mair H.-J.
, and
Polborn K.
, Synthesis , 1997 , 696 .
16.
Cabaj J.
,
Doskocz J.
,
Sołtoducho J.
, and
Chyla A.
, Heterocycles , 2006 , 68 , 137 .
17.
Semenov A.
,
Spatz J.P.
,
Moller M.
,
Lehn J.-M.
,
Sell B.
,
Schubert D.
,
Weidl C.H.
, and
Schubert U.S.
, Angew. Chem., Int. Ed. , 1999 , 38 , 2547 .
18.
Riesgo E.
,
Hu Y.-Z.
,
Bouvier F.
, and
Thummel R.P.
, Inorg. Chem. , 2001 , 40 , 2541 .
19.
Wong K.T.
,
Hung T.-S.
,
Lin Y.
,
Wu C.-C.
,
Lee G.-H.
,
Peng S.-M.
,
Chou C.H.
, and
Su Y.O.
, Org. Lett. , 2002 , 4 , 513 .
20.
Harriman A.
, and
Ziessel R.
, Coord. Chem. Rev. , 1998 , 171 , 331 .
21.
Harriman A.
, and
Ziessel R.
, Chem. Commun. , 1996 , 1707 .
22.
Kraft A.
,
Grimsdale A.C.
, and
Holmes A.B.
, Angew. Chem., Int. Ed. , 1998 , 37 , 402 .
23.
Pascal L.
,
Vanden Eynde J.J.
,
Van Haverbeke Y.
,
Dubois P.
,
Michel A.
,
Rant U.
,
Zojer E.
,
Leising G.
,
Van Dorn L.O.
,
Gruhn N.E.
,
Cornil J.
, and
Bredas J.L.
, J. Phys. Chem. B , 2002 , 106 , 6442 .
24.
Liu B.
,
Hu X.-L.
,
Liu J.
,
Zhao Y.-D.
, and
Huang Z.-L.
, Tetrahedron Lett. , 2007 , 48 , 5958 .
25.
Marzinzik A.L.
, and
Felder E.R.
, J. Org. Chem. , 1998 , 63 , 723 .
26.
Gupta K.C.
, and
Manglum P.
, Curr. Sci. , 1989 , 58 , 1196 .
27.
Forrester A.R.
,
Gill M.
, and
Thomson R.H.
, J. Chem. Soc., Perkin Trans. 1 , 1979 , 616 .
28.
Martınez A.G.
,
Fernandez A.H.
,
Alvarez R.M.
,
Losada M.C.S.
,
Vilchez D.M.
,
Subramanian L.R.
, and
Hanack M.
, Synthesis , 1990 , 881 .
29.
Muller T.J.J.
,
Braun R.
, and
Ansorge M.
, Org. Lett. , 2000 , 2 , 1967 .
30.
Seki M.
,
Kubota H.
,
Matsumoto K.
,
Kinumaki A.
,
Date T.
, and
Okamura K.
, J. Org. Chem. , 1993 , 58 , 6354 .
31.
Itami K.
,
Yamazaki D.
, and
Yoshida J.
, J. Am. Chem. Soc. , 2004 , 126 , 15396 .
32.
Bagley M.C.
,
Hughes D.D.
, and
Taylor P.H.
, Synlett , 2003 , 259 .
33.
Sreedhar B.
,
Reddy M.A.
, and
Reddy P.S.
, Synlett , 2008 , 13 , 1949 .
34.
Mao H.
,
Wan J.
, and
Pan Y.
, Tetrahedron , 2009 , 65 , 1026 .
35.
Khosropour A.R.
,
Mohammadpoor-Baltork I.
,
Ghorbankhani H.
, Catal. Commun. , 2006 , 7 , 713 .
36.
Pourghobadi Z.
,
Derikvand F.
, Chin. Chem. Lett. , 2010 , 21 (3 ), 269 .
37.
Heravi M.M.
,
Derikvand F.
,
Ranjbar L.
,
Bamoharram F.F.
, Synth. Commun. , 2010 , 40 (9 ), 1256 .
38.
Goncalves S.
,
Wagner A.
,
Mioskowski C.
, and
Baati R.
, Tetrahedron Lett. , 2009 , 50 , 274 .
39.
Kysil V.
,
Tkachenko S.
,
Khvat A.
,
Williams C.
,
Tsirulnikov S.
,
Churakovab M.
, and
Ivachtchenko A.
, Tetrahedron Lett. , 2007 , 48 , 6239 .
40.
Bian X.
,
Liu H.
,
Geng X.
,
Xie Z.
,
Li S.
, and
Wang C.
, J. Chem. Res. , 2009 , 81 .
41.
Xie Z.
,
Bian X.
,
Geng X.
,
Li S.
, and
Wang C.
, J. Chem. Res. , 2008 , 52 .
42.
Geng X.
,
Li S.
,
Bian X.
,
Xie Z.
, and
Wang C.
, ARKIVOC , 2008 , (xiv) , 50 .
43.
Jiang C.
,
Geng X.
,
Zhang Z.
,
Xu H.
, and
Wang C.
, J. Chem. Res. , 2010 , 19 .
44.
Nasielski J.
,
Standaert A.
, and
Nasielski-Hinkens R.
, Synth. Commun. , 1991 , 21 , 901 .
