Abstract
anti-9-Methoxy[3]metacyclo[3](2,6)pyridinophan-2,11-dione is obtained by the coupling reaction of 2,6-bis (bromomethyl)pyridine and 2,6-bis[2-isocyano-2-(tolylsulfonyl)ethyl]-4-tert-butylanisole in dimethylformamide (DMF) with an excess of sodium hydride, from which the corresponding syn-9-methoxy[3]metacyclo[3](2, 6)pyridinophane is synthesised via anti–syn-isomerisation during the Wolff–Kishner reduction in good yield.
Keywords
References
1.
Vögtle F.
, Cyclophane chemistry. John Wiley & Sons Ltd. , 1993 .
2.
Semmelhack M.F.
,
Harrison J.J.
,
Young D.C.
,
Gutiérrez A.
,
Rafii S.
, and
Clardy J.
, J. Am. Chem. Soc. , 1985 , 107 , 7508 .
3.
Vögtle F.
, and
Schunder L.
, Chem. Ber. , 1969 , 102 , 2677 .
4.
Shinmyozu T.
,
Inazu T.
, and
Yoshino T.
, Chem. Lett. , 1976 , 1405 .
5.
Sako K.
,
Hirakawa T.
,
Fujimoto N.
,
Shinmyozu T.
,
Inazu T.
, and
Horimoto H.
, Tetrahedron Lett. , 1988 , 29 , 6275 .
6.
Sako K.
,
Shinmyozu T.
,
Takemura H.
,
Suenaga M.
, and
Inazu T.
, J. Org. Chem. , 1992 , 57 , 6536 .
7.
Nishimura J.
,
Ohbayashi A.
,
Horiuchi Y.
,
Okada Y.
,
Namanaka Y.
, and
Oku A.
, J. Org. Chem. , 1987 , 57 , 6536 .
8.
Fukazawa Y.
,
Takeda Y.
,
Usui S.
, and
Kodama M.
, J. Am. Chem. Soc. , 1988 , 110 , 7842 .
9.
Ernst L.
, Prog. Nucl. Magn. Res. Spectrosc. , 2000 , 37 , 47 .
10.
Possel O.
, and
van Leusen A.M.
, Tetrahedron Lett. , 1977 , 4229 .
11.
van Leusen D.
, and
van Leusen A.M.
, Tetrahedron Lett. , 1977 , 4233 .
12.
Shinmyozu T.
,
Inazu T.
, and
Yoshino T.
, Mem. Fac. Sci., Kyushu Univ. Ser. C , 1985 , 15 , 79 .
13.
Osada S.
,
Miyahara Y.
,
Shinmyozu T.
, and
Inazu T.
, Mem. Fac. Sci., Kyushu Univ. Ser. C , 1993 , 19 , 39 .
14.
Osada S.
,
Miyahara Y.
,
Shimizu N.
, and
Inazu T.
, Chem. Lett. , 1995 , 1103 .
15.
Breitenbach J.
, and
Vögtle F.
, Synthesis , 1992 , 41 .
16.
Breitenbach J.
,
Ott F.
, and
Vögtle F.
, Angew. Chem. , 1992 , 104 , 360
17.Angew. Chem. Int. Ed. Engl. , 1992 , 31 , 307 .
18.
Ott F.
,
Breitenbach J.
,
Nieger M.
, and
Vögtle F.
, Chem. Ber. , 1993 , 126 , 97 .
19.
Kobiro K.
,
Takashi M.
,
Nishikawa N.
,
Kikuchi K.
,
Tobe Y.
, and
Odaira Y.
Tetrahedron Lett. , 1987 , 28 , 3825 .
20.
Kurosawa K.
,
Suenaga M.
,
Inazu T.
, and
Yoshino T.
, Tetrahedron Lett. , 1982 , 23 , 5335 .
21.
Shinmyozu T.
,
Hirai Y.
, and
Inazu T.
, J. Org. Chem. , 1986 , 51 , 1551 .
22.
Meno T.
,
Sako K.
,
Suenaga M.
,
Mouri M.
,
Shinmyozu T.
,
Inazu T.
, and
Takemura H.
, Can. J. Chem. , 1990 , 68 , 440 .
23.
Sako K.
,
Meno T.
,
Takemura H.
,
Shinmyozu T.
, and
Inazu T.
, Chem. Ber. , 1990 , 123 , 630 .
24.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1985 , 50 , 2939 .
25.
Yamato T.
,
Matsumoto J.
,
Tokuhisa K.
,
Tsuji K.
,
Suehiro K.
, and
Tashiro M.
, J. Chem. Soc., Perkin Trans. 1 , 1992 , 2675 .
26.
Tashiro M.
, and
Yamato T.
, Org. Prep. Proced. Int. , 1981 , 13 , 1 .
27.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1981 , 46 , 4556 .
28.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1983 , 48 , 1461 .
29.
Yamato T.
,
Matsumoto J.
,
Tokuhisa K.
,
Kajihara M.
,
Suehiro K.
, and
Tashiro M.
, Chem. Ber. , 1992 , 125 , 2443 .
30.
Yamato T.
,
Miyazawa A.
, and
Tashiro M.
, J. Chem. Soc., Perkin Trans. 1 , 1993 , 3127 .
31.
Yamato T.
,
Miyazawa A.
, and
Tashiro M.
, Chem. Ber. , 1993 , 126 , 2505 .
32.
Smith B.H.
, Bridged aromatic compounds. Academic Press , New York . 1964 .
33.
Vögtle F.
, and
Neumann P.
, Angew. Chem. , 1972 , 84 , 75
34.Angew. Chem. Int. Ed. Engl. , 1972 , 11 , 73 .
35.
Vögtle F.
, and
Neumann P.
, Synthesis , 1973 , 85 .
36.
Vögtle F.
, and
Höhner G.
, Top. Curr. Chem. , 1978 , 74 , 1 .
37.
Keehn P.M.
, and
Rosenfield S.M.
, Cyclophanes. Academic Press , New York , Vol. 1 , 1983 .
38.
Mitchell R.H.
, and
Boekelheide V.
, Tetrahedron Lett. , 1970 , 1197 .
39.
Mitchell R.H.
, and
Boekelheide V.
, J. Chem. Soc., Chem. Commun. , 1970 , 1555 .
40.
Anker W.
,
Bushnell G.W.
, and
Mitchell R.H.
, Can. J. Chem. , 1979 , 57 , 3080 .
41.
Mitchell R.H.
,
Carruther R.J.
,
Mazuch L.
, and
Dingle T.W.
, J. Am. Chem. Soc. , 1982 , 104 , 2544 .
42.
Mitchell R.H.
, and
Boekelheide V.
, J. Am. Chem. Soc. , 1974 , 96 , 1547 .
43.
Yamato T.
,
Tsuchihashi K.
,
Tanaka K.
,
Hirahara M.
, and
Tanaka K.
, Can. J. Chem. , 2002 , 80 , 510 .
44.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1981 , 46 , 1543 .