Abstract
A convenient and concise synthesis of 1,4,5,8-tetramethoxynaphthalene can be achieved by methylation of 2,3-dihydronaphthazarin with dimethylsulfate in the presence of phase transfer catalytic in 90.3% yield, then formylation of 1,4,5,8-tetramethoxynaphthalene can afford 2-formyl-1,4,5,8-tetramethoxynaphthalene in 96.2% yield.
References
1.
Terada A.
,
Tanoue Y.
,
Hatada A.
, and
Sakamoto H.
, Bull. Chem. Soc. Jpn. , 1987 , 60 , 205 .
2.
Ahn B.Z.
,
Baik K.U.
,
Kweon G.R.
,
Lim K.
, and
Hwang B.D.
, J. Med. Chem. , 1995 , 38 , 1044 .
3.
Hayashi M.
, Nippon Yakurigaku Zassh , 1977 , 73 , 193 .
4.
Papageorgiou V.P.
, Planta Med. , 1980 , 38 , 193 .
5.
Wagner H.
,
Kreher B.
, and
Jurcic K.
, Arzneim. Forsch./Drug Res. , 1988 , 38 , 273 .
6.
Hisa T.
,
Kimura Y.
,
Takada K.
,
Suzuki F.
, and
Takigawa M.
, Anticancer Res. , 1988 , 18 , 783 .
7.
Chang Y.S.
,
Kuo S.C.
,
Weng S.H.
,
Jan S.C.
,
Ko F.N.
, and
Teng C.M.
, Planta Med. , 1993 , 59 , 401 .
8.
Futagoishi H.
, and
Abe T.
, Cosmet. Perfum. , 1973 , 88 , 51 .
9.
Xu D.F.
,
Guan P.J.
,
Mao Z.Q.
,
Wang Z.M.
, and
Li S.S.
, Chin. J. Pharm. , 2004 , 35 , 583 .
10.
Huor R.
, and
Brassard P.
, Can. J. Chem. , 1974 , 52 , 838 .
11.
Lewis R.
, and
Paul John
, Z. Naturforsch. B , 1977 , 32 , 1473 .
12.
Zweig A.
,
Maurer A.H.
, and
Roberts B.G.
, J. Org. Chem. , 1967 , 32 , 1332 .
