Abstract
A mild and efficient method for the synthesis of thiopyrano[3,4-c]quinoline derivatives via an imino-Diels–Alder reaction of an aromatic aldehyde, 5-amino-1H-indazole or 2-aminoanthracene and tetrahydrothiopyran-4-one catalysed by iodine is described. This new procedure has the advantages of mild reaction conditions, high yields and metal-free catalysis. This is useful since quinoline and its derivatives have extensive biological activities.
References
1.
Eswaran S.
,
Adhikari A.V.
,
Shetty N.S.
, Eur. J. Med. Chem. , 2009 , 44 , 4637 .
2.
Yang C.L.
,
Tseng C.H.
,
Chen Y.L.
,
Lu C.M.
,
Kao C.L.
,
Wu M.H.
,
Tzeng C.C.
, Eur. J. Med. Chem. , 2010 , 45 , 602 .
3.
Smith P.W.
,
Wyman P.A.
,
Lovell P.
,
Goodacre C.
,
Serafinowska H.T.
,
Vong A.
,
Harrington F.
,
Flynn S.
,
Bradley D.M.
,
Porter R.
,
Coggon S.
,
Murkitt G.
,
Searle K.
,
Thomas D.R.
,
Watson J.M.
,
Martin W.
,
Wu Z.N.
,
Dawson L.A.
, Bioorg. Med. Chem. Lett. , 2009 , 19 , 837 .
4.
Kang I.J.
,
Wang L.W.
,
Hsu S.J.
,
Lee C.C.
,
Lee Y.C.
,
Wu Y.S.
,
Hsu T.A.
,
Yueh A.
,
Chao Y.S.
,
Chern J.H.
, Bioorg. Med. Chem. Lett. , 2009 , 19 , 4134 .
5.
Michel B.W.
,
Steffens L.D.
, and
Sigman M.S.
, J. Am. Chem. Soc. , 2011 , 133 , 8317 .
6.
Li M.
,
Hou Y.L.
,
Wen L.R.
, and
Gong F.M.
, J. Org. Chem. , 2010 , 75 , 8522 .
7.
Luo Y.
,
Pan X.L.
, and
Wu J.
, Org. Lett. , 2011 , 13 , 1150 .
8.
Povarov L.S.
, Russ. Chem. Rev. , 1967 , 36 , 656 .
9.
Kouznetsov V.V.
, Tetrahedron , 2009 , 65 , 2721 .
10.
Lin X.F.
,
Cui S.L.
, and
Wang Y.G.
, Tetrahedron Lett. , 2006 , 47 , 3127 .
11.
Wang X.S.
,
Li Q.
,
Wu J.R.
, and
Tu S.J.
, J. Comb. Chem. , 2009 , 11 , 433 .
12.
Wang X.S.
,
Li Q.
,
Yao C.S.
, and
Tu S.J.
, Eur. J. Org. Chem. , 2008 , 3513 .
13.
Yin M.Y.
,
Wang W.
,
Zhang M.M.
, and
Wang X.S.
, J. Chem. Res. , 2011 , 35 , 513 .
