Abstract
The condensation and addition reactions of aromatic aldehydes and 4,6-dihydroxypyrimidine or 2,4-dihydroxy-6-aminopyrimidine in water in the presence of triethylbenzylammonium chloride (TEBAC) afford a one-pot synthesis of 5,5′-(arylmethylene)bis[6-hydroxypyrimidine-4(3H)-one]s and 5,5′-(arylmethylene)bis[6-aminopyrimidine-2,4 (1H,3H)-dione]s. These compounds were characterised by elemental analysis and IR and 1H NMR spectra and further confirmed by a single crystal X-ray diffraction analysis.
Keywords
References
1.
Bradshaw T.K.
, and
Hutchison D.W.
, Chem. Soc. Rev. , 1977 , 6 , 43 .
2.
Sasaki T.
,
Minamoto K.
,
Suzuki T.
, and
Yamashita S.
, Tetrahedron , 1980 , 36 , 865 .
3.
Prajapati D.
,
Bhuyan P.J.
, and
Sandhu J.S.
, J. Chem. Soc., Perkin Trans. I , 1988 , 607 .
4.
Bhuyan P.J.
,
Borah H.N.
, and
Sandhu J.S.
, J. Chem. Soc., Perkin Trans. I , 1999 , 3083 .
5.
Marumoto R.
, and
Furukawa Y.
, Chem. Pharm. Bull. , 1997 , 25 , 2974 .
6.
Griengl R.
,
Wack E.
,
Schwarz W.
,
Streicher W.
,
Rosenwirth B.
, and
Clercq E.D.
, J. Med. Chem. , 1987 , 30 , 1199 .
7.
Clercq E.D.
, and
Bernaertes R.
, J. Biol. Chem. , 1987 , 262 , 14905 .
8.
Jones A.S.
,
Sayers J.R.
,
Walker R.T.
, and
Clercq E.D.
, J. Med. Chem. , 1988 , 31 , 268 .
9.
Mitsuya H.
,
Yarchoan R.
, and
Broder S.
, Science , 1990 , 249 , 1533 .
10.
Pontikis R.
, and
Monneret C.
, Tetrahedron Lett. , 1994 , 35 , 4351 .
11.
Heidelberger C.
, and
Arafield F.
, J. Cancer Res. , 1963 , 23 , 1226 .
12.
Baba M.
,
Pauwels R.
,
Herdwig P.
,
Clercq E.D.
,
Desmyster J.
, and
Vandepulfe M.
, Biochem. Biophys. Res. Commun. , 1987 , 142 , 128 .
13.
Clercq E.D.
, J. Med. Chem. , 1986 , 29 , 1561 .
14.
Jones A.S.
,
Verhalst G.
, and
Walker R.T.
, Tetrahedron Lett. , 1974 , 15 , 4415 .
15.
Hirota K.
,
Kitade Y.
,
Senda S.
,
Halat M.J.
,
Watanabe K.A.
, and
Fox J.J.
, J. Org. Chem. , 1981 , 46 , 846 .
16.
Su T.L.
,
Huang J.T.
,
Burchanal J.H.
,
Watanabe K.A.
, and
Fox J.J.
, J. Med. Chem. , 1986 , 29 , 709 .
17.
Prajapati D.
, and
Sandhu J.S.
, Synthesis , 1988 , 342 .
18.
Jiang J.B.
, and
Roberts J.
, J. Heterocyclic Chem. , 1985 , 22 , 159 .
19.
Azizian J.
,
Mohammadizadeh M.R.
,
Teimouri F.
,
Mohammadi A.A.
, and
Karimi A.R.
, Synth. Commun. , 2006 , 36 , 3631 .
20.
Moskvin A.V.
,
Meshcheryakov M.P.
,
Reznikova N.R.
,
Fedorova E.V.
, and
Ivin B.A.
, Russ. J. Gen. Chem. , 2002 , 72 , 1473 .
21.
Amato J.
, Science , 1993 , 259 , 1538 .
22.
Illman D.L.
, Chem. Eng. News , 1993 , 71 , 5 .
23.
Illman D.L.
, Chem. Eng. News , 1994 , 72 , 22 .
24.
Li C.J.
, and
Chang T.H.
, Organic reactions in aqueous media , Wiley , New York , 1997 .
25.
Fringuell F.
,
Piematti O.
,
Pizzo F.
, and
Vaccaro L.
, Eur. J. Org. Chem. , 2001 , 439 .
26.
Stinson S.C.
, Chem. Eng. News , 1996 , 74 , 39 .
27.
Breslow R.
, and
Rideout D.C.
, J. Am. Chem. Soc. , 1980 , 102 , 7816 .
28.
Breslow R.
, Acc. Chem. Res. , 1991 , 24 , 159 .
29.
Li C.J.
, Chem. Rev. , 1993 , 93 , 2023 .
30.
Ballini R.
, and
Bosica G.
, Tetrahedron Lett. , 1996 , 37 , 8027 .
31.
Ballini R.
,
Bosica G.
, and
Mecozzi T.
, Tetrahedron , 1997 , 53 , 1341 .
32.
Meijier A.
,
Otto S.
, and
Engberts J.B.F.N.
, J. Org. Chem. , 1998 , 63 , 8989 .
33.
Bigi F.
,
Chesini L.
,
Maggi R.
, and
Sartori G.
, J. Org. Chem. , 1999 , 64 , 1033 .
34.
Bigi F.
,
Carloni S.
,
Ferrari L.
,
Maggi R.
,
Mazzacani A.
, and
Sartori G.
, Tetrahedron Lett. , 2001 , 42 , 5203 .
35.
Fringuelli F.
,
Pani G.
,
Piermatti O.
, and
Pizzo F.
, Tetrahedron , 1994 , 50 , 1499 .
36.
Shi D.Q.
,
Chen J.
,
Zhuang Q.Y.
,
Wang X.S.
, and
Hu H.W.
, J. Chem. Res.(S) , 2003 , 674 .
37.
Wang J.
,
Shi D.Q.
,
Zhuang Q.Y.
,
Wang X.S.
, and
Hu H.W.
, J. Chem. Res. , 2004 , 818 .
38.
Shi D.Q.
,
Niu L.H.
, and
Zhuang Q.Y.
, J. Chem. Res. , 2005 , 648 .
39.
Shi D.Q.
,
Niu L.H.
,
Wang X.S.
,
Zhuang Q.Y.
, and
Zhang Y.
, J. Chem. Res. , 2005 , 224 .
40.
Sheldrick G.M.
, SHELXL-97, Program for the Solution of Crystal Structures University of Gottingen , 1997 .
41.
Sheldrick G.M.
, SHELXL-97, Program for the Refinement of Crystal Structures University of Gottingen , 1997 .
