Abstract
A series of chromen-2-one derivatives was synthesised by the reaction of 4-hydroxy-6-methyl-2H-pyran-2-one with substituted 2-hydroxybenzaldehydes catalysed by L-proline. This protocol has the advantages of easy workup mild reaction conditions and high yields.
References
1.
Singer L.A.
, and
Kong N.P.
, J. Am. Chem. Soc. , 1966 , 88 , 5213 .
2.
El Grody A.M.
,
Abdel Latif M.S.
, and
El Hady N.A.
, Molecules , 2001 , 6 , 519 .
3.
Al Haiza M.A.
,
Mostsfa M.S.
, and
El Kady M.Y.
, Molecules , 2003 , 8 , 275 .
4.
O'Kennedy R.
, and
Thornes R.D.
, Coumarins: biology, applications and mode of action , Wiley & Sons , Chichester , 1997 .
5.
Zahradnik M.
, The production and application of fluorescent brightening agents , Wiley & Sons , New York , 1992 .
6.
Murray R.D.H.
,
Mendez J.
, and
Brown S.A.
, The natural coumarins: occurrence, chemistry and biochemistry , Wiley & Sons , New York , 1982 .
7.
Potdar M.K.
,
Mohile S.S.
, and
Salunkhe M.M.
, Tetrahedron Lett. , 2001 , 42 , 9285 .
8.
Pechmann H. v.
, and
Duisberg C.
, Chem. Ber. , 1884 , 17 , 929 .
9.
Jonson J.R.
, Org. React. , 1942 , 1 , 210 .
10.
Jones G.
, Org. React. , 1967 , 15 , 204 .
11.
Brufola G.
,
Fringuelli F.
,
Piermatti O.
, and
Pizzo F.
, Heterocycles , 1996 , 43 , 1257 .
12.
Shriner R.L.
, Org. React. , 1942 , 1 , 1 .
13.
Narasimahan N.S.
,
Mali R.S.
, and
Barve M.V.
, Synthesis , 1979 , 906 .
14.
Yavari I.
,
Hekmat-Shoar R.
, and
Zonouzi A.
, Tetrahedron Lett. , 1998 , 39 , 2391 .
15.
Russell A.
, and
Frye J.R.
, Org. Synth. , 1941 , 21 , 22 .
16.
Woods L.L.
,
Sapp J.
, J. Org. Chem. , 1962 , 27 , 3703
17.
Alcaide B.
,
Almendros P.
,
Luna A.
, and
Torres M.R.
, J. Org. Chem. , 2006 , 71 , 4818 .
18.
Janey J.M.
,
Hsiao Y.
, and
Armstrong J.D.
III
, J. Org. Chem. , 2006 , 71 , 390 .
19.
Kotrusz P.
, and
Toma S.
, Arkivoc , 2006 , 100 .
20.
Ramachary D.B.
,
Chowdari N.S.
, and
Barbas C.F.
III
, Angew. Chem. , 2003 , 115 , 4365 .
21.
Hossein A.O.
,
Elham R.
, and
Majid M.H.
, J. Chem. Res. , 2006 , 246 .
22.
Mabry J.
, and
Ganem B.
, Tetrahedron Lett. , 2006 , 47 , 55 .
23.
Kumar A.
, and
Maurya R.A.
, Tetrahedron , 2007 , 63 , 1946 .
24.
Shi C.L.
,
Shi D.Q.
,
Kim S.H.
,
Huang Z.B.
,
Ji S.J.
, and
Ji M.
, Tetrahedron , 2008 , 64 , 2425 .
25.
Shi C.L.
,
Shi D.Q.
,
Kim S.H.
,
Huang Z.B.
, and
Ji M.
, Aust. J. Chem. , 2008 , 61 , 547 .
26.
Svetlik J.
,
Pronayava N.
, and
Hanus V.
, J. Heterocyclic Chem. , 2000 , 37 , 395 .
27.
Wang X.S.
,
Zeng Z.S.
,
Zhang M.M.
,
Shi D.Q.
, and
Tu S.J.
, J. Chem. Res. , 2006 , 602 .