Abstract
Seven new tetracyclic diesters [dialkyl 1-anilino-4-aryl-3-(1-hydroxynaphthalen-2-yl)-4-oxobut-1-ene-1,2-dicarboxylates] have been prepared in good yield by a one-pot four-component reaction between enamine intermediates (as Michael donors) generated from aniline and a dialkyl acetylenedicarboxylate and α,β-unsaturated γ-dicarbonyl intermediates (as Michael acceptors) generated from α-naphthol and an arylglyoxal without using a catalyst in ethanol at reflux conditions.
References
1.
Sibi M.P.
, and
Manyem S.
, Tetrahedron , 2000 , 56 , 8033 .
2.
Berner O.M.
,
Tedeschi L.
, and
Enders D.
, Eur. J. Org. Chem. , 2002 , 2002 , 1877 .
3.
Christoffers J.
, and
Baro A.
, Angew. Chem., Int. Ed. , 2003 , 42 , 1688 .
4.
Notz W.
,
Tanaka F.
, and
Barbas C. F.
, Acc. Chem. Res. , 2004 , 37 , 580 .
5.
Ballini R.
,
Bosica G.
,
Fiorini D.
,
Palmieri A.
, and
Petrini M.
, Chem. Rev. , 2005 , 105 , 933 .
6.
Sulzer-Mossé S.
, and
Alexakis A.
, Chem. Commun. , 2007 , 3123 .
7.
Bergmann E.D.
,
Ginsberg D.
, and
Pappo R.
, Organic reactions. John Wiley and Sons , New York , 1959 , Vol. 10 , p. 179 .
8.
Grossman R.B.
, Synlett , 2001 , 2001 , 13 .
9.
Rodriguez J.
, Synlett , 1999 , 1999 , 505 .
10.
Varner M.A.
, and
Grossman R. B.
, Tetrahedron , 1999 , 55 , 13867 .
11.
Christoffers J.
, Synlett , 2001 , 2001 , 723 .
12.
Kobayashi S.
, Synlett , 1994 , 1994 , 689 .
13.
Mañas M.M.
,
Marquet J.
, and
Vallribera A.
, Tetrahedron , 1996 , 52 , 3377 .
14.
Shibasaki M.
,
Sasai H.
, and
Arai T.
, Angew. Chem., Int. Ed. Engl. , 1997 , 36 , 1236 .
15.
Christoffers J.
, Eur. J. Org. Chem. , 1998 , 1998 , 1259 .
16.
Hickmott P.W.
,
Miles G. J.
,
Sheppard G.
,
Urbani R.
, and
Yoxall C. T.
, J. Chem. Soc. Perkin Trans. 1 , 1973 , 1514 .
17.
Hickmott P.W.
,
Hopkins B. J.
,
Sheppard G.
, and
Barraclough D. J.
, J. Chem. Soc., Perkin Trans. 1 , 1972 , 1639 .
18.
Ye J.-H.
,
Ling K.-Q.
,
Zhang Y.
,
Li N.
, and
Xu J.-H.
, J. Chem. Soc., Perkin Trans., 1 , 1999 , 2017 .
19.
Giardini A.
,
Lesma G.
,
Passarella D.
,
Perez M.
, and
Silvani A.
, Synlett , 2001 , 2001 , 132 .
20.
Stamhuis E.J.
, and
Maas W.
, J. Org. Chem. , 1965 , 30 , 2156 .
21.
Maas W.
,
Janssen M. J.
,
Stamhuis E. J.
, and
Wynberg H.
, J. Org. Chem. , 1967 , 32 , 1111 .
22.
Mehrabi H.
, and
Saleki T.
, J. Chem. Res. , 2015 , 39 , 195 .
23.
Mehrabi H.
, and
Baniasad-Dashtabi M.
, J. Chem. Res. , 2015 , 39 , 294 .
24.
Mehrabi H.
, and
Esfandiarpour Z.
, J. Sulfur. Chem. , 2015 , 36 , 583 .
25.
Riley H.A.
, and
Gray A. R.
, Organic Syntheses. Wiley & Sons : New York , 1943 , Collected Vol. 2 , p. 509 .