Abstract
The proportion of 5-/7- substituted coumarins formed in the Pechmann synthesis from meta-substituted phenols and malic acid and ethyl acetoacetate under a variety of reaction conditions, with product analysis by 1H and 13C NMR spectroscopy, is reported.
Keywords
References
1.
Osborne A. G.
, Tetrahedron , 1981 , 37 , 2021 .
2.
von Pechmann H.
, Ber. , 1884 , 17 , 929 .
3.
Setna S.
, and
Phadke R.
, Org. Reacts. , 1953 , 7 , 1 .
4.
Clayton A.
, J. Chem. Soc. , 1908 , 93 , 2016 .
5.
Osborne A.G.
, Org. Magn. Reson. , 1989 , 27 , 348 .
6.
Molyneux R.J.
, and
Jurd L.
, Austral. J. Chem. , 1974 , 27 , 2697 .
7.
March J.
, Advanced Organic Chemistry , Wiley , New York , 4th edn, 1992 , p. 433 .
8.
Okogun J.I.
,
Enyenihi V. U.
, and
Ekong D. E. U.
, Tetrahedron , 1978 , 34 , 1221 .
9.
Osborne A.G.
, Tetrahedron , 1983 , 39 , 1523 .
10.
Blatchly R.A.
,
Greeley M. A.
, and
Markgraf J. H.
, Heterocycles , 1989 , 29 , 2345 .
11.
Knorr L.
, Annalen , 1888 , 245 , 357 .