Abstract
A convenient and efficient synthetic method of the important intermediate naphthazarin is presented starting from 1, 4, 5, 8-tetramethoxynaphthalene in an overall yield of 87%. Compared with the reported synthesis, this method has several advantages. Firstly, the reaction conditions are milder; secondly, the workup of each step is simpler and the yield is considerably higher; thirdly, all the reactions involved in the method are more suitable for large-scale preparations.
References
1.
Ernst-Russell M.A.
,
Elix J.A.
,
Chai C.L.L.
,
Willis A.C.
,
Hamada N.
, and
Nash T.H.
III
, Tetrahedron Lett. , 1999 , 40 , 6321 .
2.
Tanaka H.
,
Yoshikoka T.
,
Shimauchi Y.
,
Yoshimoto A.
, and
Ishikura T.
, Tetrahedron Lett. , 1984 , 25 , 3351 .
3.
Burns C.J.
,
Gill M.
, and
Saubern S.
, Aust. J. Chem. , 1991 , 44 , 1427 .
4.
Arnone A.
, and
Merlini L.
, Synth. Commun. , 2007 , 37 , 2569 .
5.
Papageorgiou V.P.
,
Assimopoulou A.N.
,
Couladouros E.A.
,
Hepworth D.
, and
Nicolaou K.C.
, Angew. Chem. Int. Ed. , 1999 , 38 , 270 .
6.
Perez Y.
,
Zarcero S.M.
, and
Sierra I.
, Inorg. Chim. Acta , 2007 , 360 , 607 .
7.
Yakubovskaya A.Y.
,
Pokhilo N.D.
, and
Anufriev V.F.
, J. Pharmac. Chem. , 2009 , 43 , 396 .
8.
Tandon V.K.
, and
Yadav D.B.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 5324 .
9.
Zhou J.
,
Duan L.
,
Ren X.M.
,
Zhang Z.
, and
Zhou F.T.
, Bioorg. Med. Chem. Lett. , 2009 , 19 , 5091 .
10.
Tandon V.K.
,
Yadav D.B.
, and
Vaish M.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 3463 .
11.
Singh I.
,
Moore R.E.
,
Chang C.W.J.
,
Ogata R.T.
, and
Scheuer P.J.
, Tetrahedron. 1968 , 24 , 2969 .
12.
Huot R.
, and
Brassard P.
, Can. J. Chem. , 1974 , 54 , 838 .
13.
Waldmann H.
, and
Ulsperger E.
, Chem. Ber. , 1950 , 83 , 178 .
14.
Mital A.
, and
Negi V. S.
, J. Med. Chem. , 2008 , 4 , 492 .
15.
Motoji K.
,
Fuyuhiko M.
, and
Shiro T.
, Tetrahedron. 1988 , 44 , 5713 .
16.
Terada A.
,
Tanoue Y.
, and
Hatada A.
, Bull. Chem. Soc. Jpn. , 1987 , 60 , 205 .
17.
Menegazzo I.
,
Moro S.
, and
Sheeba V.
, Tetrahedron Lett. , 2000 , 41 , 6631 .
18.
Menegazz I.
,
Sandona G.
,
Moro S.
,
Sheeba V.
, and
Zagotto G.
, Tetrahedron Lett. , 2000 , 41 , 6631 .
19.
Wang R.B.
,
Zheng X.G.
,
Zhou W.
, and
Li S.S.
, J. Chem. Res. , 2010 , 9 , 520 .
20.
Bruce D.B.
, and
Thompson R.H.
, J. Chem. Soc. , 1955 , 1089 .
21.
Escobar C.
,
Farian F.
,
Utrilla R.M.
, and
Paredes M.C.
, J. Chem. Res. , 1980 , 156 .
22.
Laatsch H.
, Liebigs Ann. Chem. , 1986 , 10 , 1655 .
23.
Farina F.
,
Tamayo M.L.
, and
Suarez C.
, Anal. Real Soc. Espan. Fis. Quim. (Madrid ), 1963 , 59 , 167 .
