Abstract
Isoxazoles have significant hypoglycaemic, immunosuppressive, anti-inflammatory, and anti-bacterial activities. A convenient high yielding procedure for the one-pot synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones by the condensation of ethyl acetoacetate, hydroxylamine hydrochloride and aromatic aldehydes in the presence of sodium silicate pentahydrate as an efficient catalyst in water at room temperature is described.
References
1.
Conti P.
,
Dallanoce C.
,
Amici M.D.
,
Micheli C.D.
, and
Klotz K.N.
, Bioorg. Med. Chem. , 1998 , 6 , 401 .
2.
Gordaliza M.G.
,
Faircloth T.
,
Castro M.A.
,
del Corral J.M.M.
,
López-Vázquez M.L.
, and
San Feliciano A.
, J. Med. Chem. , 1996 , 39 , 2865 .
3.
Kwon T.
,
Heimann A.S.
,
Oriaku E.T.
, and
Yoon K.
, J. Med. Chem. , 1995 , 38 , 1048 .
4.
Kang Y.Y.
,
Shin K.J.
,
Yo K.H.
,
Seo K.J.
,
Hong C.Y.
,
Lee C.S.
,
Park S.Y.
,
Kim D.J.
, and
Park S.W.
, Bioorg. Med. Chem. Lett. , 2000 , 10 , 95 .
5.
Abbiati G.
,
Beccalli E.M.
,
Broggini G.
, and
Zoni C.
, Tetrahedron , 2003 , 59 , 9887 .
6.
Cocivera M.
,
Emo A.
,
Chen H.E.
, and
Vaish S.
, J. Am. Chem. Soc. , 1976 , 98 , 7362 .
7.
Villemin D.
,
Martin B.
, and
Garrigues B.
, Synth. Commun. , 1993 , 23 , 2251 .
8.
Zhang Y.Q.
,
Wang C.
,
Zhang M.Y.
,
Cui P.L.
,
Li Y.M.
,
Zhou X.
, and
Li J.C.
, Chin. J. Org. Chem. , 2008 , 28 , 914 .
9.
Cheng Q.F.
,
Liu X.Y.
,
Wang Q.F.
,
Liu L.S.
,
Liu W.J.
,
Lin Q.
, and
Yang X.J.
, Chin. J. Org. Chem. , 2009 , 29 , 1267 .
10.
Zhang Y.Q.
,
Ma J.J.
,
Wang C.
,
Li J.C.
,
Zhang D.N.
,
Zang X.H.
, and
Li J.
, Chin. J. Org. Chem. , 2008 , 28 , 141 .
11.
Vail J.G.
, Soluble silicates: their properties and uses , Reinhold Publishing , New York , 1952 , vols. 1-2 .
12.
Heravi M.M.
,
Khorshidi M.
,
Beheshtia Yahia. Sh.
, and
Baghernejad B.
, B. Korean Chem. Soc. , 2010 , 31 , 1343 .
13.
Liu Q.
,
Ai H.M.
, and
Li Z.
, Ultrason. Sonochem. , 2011 , 18 , 477 .
14.
Domling A.
, and
Ugi I.
, Angew. Chem. Int. Ed. , 2000 , 39 , 3168 .
15.
Kappe C.O.
, Curr. Opin. Chem. Biol. , 2002 , 6 , 314 .
16.
Domling A.
, Curr. Opin. Chem. Biol. , 2002 , 6 , 306 .
