Abstract
Thermal condensation of 2′-hydroxyacetophenones 1a–e with phenylacetic acid 2a in refluxing diphenyl ether gives 4-methyl-3-phenylcoumarins 3a–e. Similarly, reaction of 2-hydroxybenzaldehydes 1f–m and 2-hydroxybenzo-phenones 1n–p with phenylacetic acids 2a–d gives the corresponding 3-arylcoumarins 3f–m and 3-aryl-4-phenylcoumarins 3n–p respectively. Formation of esters 4 and 5 and benzofuran 6 is also observed.
References
1.
Neelakantan S.
,
Raman P.V.
, and
Tinabaye A.
, Ind. J. Chem. , 1982 , 21B , 256 .
2.
Phansalkar M.S.
,
Deshmukh K.K.
,
Kelkar S.L.
, and
Wadia M.S.
, Ind. J. Chem. , 1987 , 26B , 562 .
3.
Awasthi A.K.
, and
Tewari R.S.
, Synthesis , 1986 , 1061 .
4.
Mohanty S.
,
Makrandi J.K.
, and
Grover S.K.
, Ind. J. Chem. , 1989 , 28B , 766 .
5.
Hans N.
,
Singhi M.
,
Sharma V.
, and
Grover S.K.
, Ind. J. Chem. , 1996 , 35B , 1159 .
6.
Kamat S.P.
,
Sardesai L.G.
, and
Paknikar S.K.
, Ind. J. Chem. , 1984 , 23B , 892 .
7.
Kamat S.P.
, and
Paknikar S.K.
, Ind. J. Chem. , 1985 , 24B , 38 .
8.
Sardesai L.G.
,
Paknikar S.K.
,
Bates R.B.
,
Siahaan T.J.
,
Kane V.V.
, and
Mishra P.K.
, Heterocycles , 1987 , 26 , 2941 .
9.
Jain N.
,
Devi N.
, and
Krishnamurthy H.G.
, Ind. J. Chem. , 1994 , 33B , 1085 .
10.
Narasimhan N.S.
,
Mali R.S.
, and
Barve M.V.
, Synthesis , 1979 , 906 .
11.
Ray S.
,
Grover P.K.
, and
Anand N.
, Ind. J. Chem. , 1971 , 9 , 619 .
12.
Sharma I.
, and
Ray S.
, Ind. J. Chem. , 1988 , 27B , 374 .
13.
Arventiev B.
,
Strul M.
, and
Wexler H.
, Acad. Rep. Populare, Romine, Fidiala, Isai, studii cecetari, stint. Chim. 1960 , 11 , 63; Chem. Abstr., 1961, 55, 15452a.
14.
Buu-Hoi N.P.
, and
Eckert B.
, J. Org. Chem. , 1954 , 19 , 1391 .
15.
Mitra J.
, and
Mitra A.K.
, Ind. J. Chem. , 1996 , 35B , 588 .
16.
Wulfson N.S.
,
Zaretskii V.I.
, and
Zaikin V.G.
, Bull. Acad Sci, U.S.S.R. Chem. Div. , 1963 , 2046; Chem. Abstr., 1964, 60 , 10040a.
17.
Barnes C.S.
, and
Occolowitz J.L.
, Aust. J. Chem. , 1964 , 17 , 975 .
18.
Murthy V.V.S.
,
Sampathkumar P.S.
, and
Seshadri T.R.
, Ind. J. Chem. , 1972 , 10 , 19 .
19.
Tanaka F.
,
Node M.
,
Tanaka K.
,
Mizuchi M.
,
Hosoi S.
,
Nakayama M.
,
Taga T.
, and
Fuji K.
, J. Am. Chem. Soc. , 1995 , 117 , 12159 .