Abstract
Through lithiation and electrophilic substitution of three calix[4]pyrroles, a series of new calix[4]pyrrole derivatives were synthesised. The derivatives were hydrolysed to produce acids and, under base catalysis, new esters were formed. Thus calix[4]pyrroles with an active functional group were obtained. The optimum reaction and purification conditions were investigated. The binding properties of the new derivatives with anions was examined.
References
1.
Shao S.J.
,
Guo Y.
,
He L.J.
,
Jiang S.X.
, and
Yu X.D.
, Tetrahedron Lett. , 2003 , 44 , 2175 .
2.
Miyaji H.
,
Sato W.
, and
Sessler J.L.
, Angew. Chem. Int. Ed. , 2000 , 39 , 1777 .
3.
Nielsen K.A.
,
Jeppesen J.O.
,
Levillain E.
, and
Becher J.
, Angew. Chem. Int. Ed. , 2003 , 42 , 187 .
4.
Sessler J.L.
,
Gale P.A.
, and
Genge J.W.
, Chem. Eur. J. 1998 , 4 , 1095 .
5.
Warriner C.N.
,
Gale P.A.
, and
Light M.E.
, Chem. Commun. , 2003 , 12 , 1810 .
6.
Sessler J.L.
,
Kral V.
,
Shishkanova T.V.
, and
Gale P.A.
, Proc. Nat. Acad. Sci. , 2002 , 99 , 4848 .
7.
Sessler J.L.
,
Camiolo S.
, and
Gale P.A.
, Coord. Chem. Rev. , 2003 , 240 , 17 .
8.
Lee E.C.
,
Park Y.K.
,
Kim J.H.
,
Hwang H.
,
Kim Y.R.
, and
Lee C.H.
, Tetrahedron Lett. , 2002 , 43 , 9493 .
9.
Nagarajan A.
,
Ka J.W.
, and
Lee C.H.
, Tetrahedron , 2001 , 51 , 7323 .
10.
Anzenbacher Pavel
Jr.
,
Karolina J.
,
Shriver J.A.
,
Miyaji H.
,
Lynch V.M.
,
Sessler J.L.
, and
Gale P.A.
, J. Org. Chem. , 2000 , 65 , 7641 .
11.
Gale P.A.
,
Sessler J.L.
,
Allen W.E.
,
Tvermoes N.A.
, and
Lynch V.
, Chem. Commun. , 1997 , 665 .
12.
Sessler J.L.
,
Andrievsky A.
,
Gale P.A.
, and
Lynch V.
, Angew. Chem. Int. Ed. Engl. , 1996 , 35 , 2782 .
13.
Benesi H.A.
, and
Hildebrand J.H.
, J. Am. Chem. Soc. , 1949 , 71 , 2703 .
14.
Shao S.J.
,
Yu X.D.
, and
Cao S.Q.
, Chin. Chem. Lett. , 1999 , 10 , 193 .
15.
Brown W.H.
, and
Hutchinson B.J.
,
Mackinnon M.H.
, Can. J. Chem. , 1971 , 49 , 4017 .
16.
Littler B.J.
,
Miller M.A.
,
Hung C.H.
,
Wagner R.W.
,
O'Shea D.F.
,
Boyle P.D.
, and
Lindsey J.S.
, J. Org. Chem. , 1999 , 64 , 1391 .