Abstract
In the system of K2CO3/KI/acetone, eight p-tert-butylcalix[n]arene amide products (n = 6, 8) were prepared by the O-alkylation of calixarenes with N, N-dialkyl α-chloroacetamides in high yields (HNR2 = dipropylamine, isopropylamine, pepridine, morphine). These amide products can also be synthesised by the amination reaction of the correspond ethyl calix[n]aryl acetates.
References
1.
Bohmer V.
, Angew. Chem. Int. Ed. Engl. , 1995 , 34 , 713 .
2.
Rondelez Y.
,
Bertho G.
, and
Reinaud O.
, Angew. Chem. Int. Ed Engl. , 2002 , 41 , 1044
3.
Halouani H.
,
Dumazet-Bonnamour I.
,
Duchamp C.
,
Bavoux C.
,
Ehlinger N.
,
Perrin M.
, and
Lamartine R.
, Eur. J. Org. Chem. 2002 , 4202 .
4.
Casnati A
,
Barboso S.
,
Rouquett H.
,
Schwing-Weill M. J.
,
Arnaud-Neu F.
,
Dozol J. F.
, and
Ungaro R.
, J. Am. Chem. Soc. , 2001 , 123 , 12182 .
5.
Jabin I.
, and
Reinaud O.
, J. Org. Chem. , 2003 , 68 , 3416 .
6.
Belhamel K.
,
Dzung Nguyen T. K.
,
Benamor M.
, and
Ludwig R.
, Eur. J. Inorg. Chem. , 2003 , 4110 .
7.
Arduini A.
,
Ghindini E.
,
Pochini A.
,
Ungaro R.
,
Andreetti G. D.
,
Calestani G.
, and
Ugozzoli F.
, J. Inclo. Phenom. Mol. Reconit. Chem. , 1988 , 6 , 119 .
8.
Sabbatini N
,
Guardigli M
,
Mecati A
, and
Balzani V
, J. Chem. Soc., Chem. Commun. 1990 , 878 .
9.
Falana O.M.
,
Koch H. F.
,
Roundhill D. M.
,
Lumetta G. L.
, and
Hay B. P.
, J. Chem. Soc., Chem. Commun. , 1998 , 503 .
10.
Stastny V.
,
Lhotak P.
,
Michlova V.
,
Stibor I.
, and
Sykora J.
, Tetrahedron , 2002 , 58 , 7207 .
11.
Gutsche C.D.
;
Dhawan B.
,
Leonis M.
, and
Stewant D.
, Org. Syth. 1990 . 68 . 238 .
12.
Arnaud-Neu F
,
Collins E. M.
,
Deasy M.
, and
Ferguson G.
, J. Amer. Chem. Soc. , 1989 , 111 , 8681 .
13.
Speziale A.J.
, and
Hamm P. C.
, J. Am. Chem. Chem. Soc. , 1956 . 78 . 2556 .
