Abstract
Cupric chloride showed efficient catalytic activity for the cross coupling reaction of arylboronic acids and (hydroxyi mino)ethylcoumarins at room temperature in the presence of NEt3 as base. A simple and convenient protocol for the synthesis of O-aryloxime ethers having the highly base sensitive coumarin nucleus is reported. O-Aryloxime ethers are important as they provide access to scaffolds for the generation of various biologically active compounds. They are potential precursors to benzofurans and benzisoxazoles.
References
1.
Sheradsky T.
, Tetrahedron Lett. , 1996 , 43 , 5225 .
2.
Castellino A.J.
, and
Rapoport A.J.
, J. Org. Chem. , 1984 , 49 , 4399 .
3.
Shutske G.M.
, and
Kapples G.M.
, J. Heterocycl. Chem. , 1989 , 26 , 1293 .
4.
Verma1 A.
,
Srivastava S.
,
Sane1 S.A.
,
Marrapu V.K.
,
Srinivas N.
,
Yadav M.
,
Bhandari K.
, and
Gupta S.
, Acta Trop. , 2011 , 117 , 157 .
5.
Villani F.J.
,
Tavares R.F.
, and
Ellis C.A.
, J. Pharm. Sci. , 1969 , 58 , 138 .
6.
Kochhar M.M.
,
Williams B.B.
, and
Fan J.H.
, J. Pharm. Sci. , 1969 , 58 , 1382 .
7.
Wylie B.B.
,
Isaacson E.I.
, and
Delgado J.N.
, J. Pharm. Sci. , 1965 , 54 , 1373 .
8.
Pillaia A.D.
,
Rathod P.D.
,
Franklin P.X.
,
Padh H.
, and
Vasub K.K.
, Biochem. Biophys. Res. Commun. , 2004 , 317 , 1067 .
9.
Rad M.N.S.
,
Nezhad K.A.
,
Karimitabar F.
, and
Behrouz S.
, Synthesis , 2010 , 1724 .
10.
Goda H.
,
Ihara H.
,
Hirayama C.
, and
Sato M.
, Tetrahedron Lett. , 1994 , 35 , 1565 .
11.
Murray R.D.H.
,
Mendez J.
, and
Brown S.A.
, The natural coumarins. occurrence, chemistry and biochemistry , John Wiley and Sons : Chichester , 1982 .
12.
Chimichi S.
,
Boccalini M.
,
Cosimelli B.
,
Viola G.
,
Vedaldi D.
, and
Dall'Acque F.
, Tetrahedron Lett. , 2002 , 43 , 7473 .
13.
Riveiro M.E.
,
De Kimpe N.
,
Moglioni A.
,
Vázquez R.
,
Monczor F.
,
Shayo C.
, and
Davio C.
, Curr. Med. Chem. , 2010 , 17 , 1325 .
14.
Hwu J.R.
,
Singha R.
,
Hong S.C.
,
Chang Y.H.
,
Das A.R.
,
Vliegen I.
,
Clercq E.D.
, and
Neyts J.
, Antiviral Res. , 2008 , 77 , 157 .
15.
Lam P.Y.S.
,
Clark C.G.
,
Saubern S.
,
Adams J.
,
Winters M.P.
,
Chan D.M.T.
, and
Combs A.
, Tetrahedron Lett. , 1998 , 39 , 2941 .
16.
Chan D.M.T.
,
Monaco K.L.
,
Wang R.-P.
, and
Winters M.P.
, Tetrahedron Lett. , 1998 , 39 , 2933 .
17.
Evans D.A.
,
Katz J.L.
, and
West T.R.
, Tetrahedron Lett. , 1998 , 39 , 2937 .
18.
Chan D.M.T.
,
Monaco K.L.
,
Li R.
,
Bonne D.
,
Clark C.G.
,
Lam P.Y.S.
, Tetrahedron Lett. , 2003 , 44 , 3863 .
19.
Maiti D.
, and
Buchwald S.L.
, J. Org. Chem. , 2010 , 75 , 1791 .
20.
Mann G.
, and
Hartwig J.F.
, Tetrahedron Lett. , 1997 , 38 , 8005 .