Abstract
A highly efficient procedure for preparing 2-acylpyrroles and its derivatives is described. The products were obtained through regioselective Friedel–Crafts reactions of pyrroles and its derivatives with alkyl or aryl acid chlorides catalysed by zinc oxide under solvent-free conditions. This method has the advantages of green chemistry, operational simplicity, solvent-free conditions, and recoverable catalyst.
References
1.
Joule J.A.
,
Mills K.
, and
Smith D.F.
, Heterocyclic chemistry , 3rd edn., Stanley Thornes : Cheltenham , 1998 .
2.
Posner G.H.
, Angew. Chem. Int. Ed. Engl. , 1978 , 17 , 487 .
3.
McKillop A.
, and
Young D.W.
, Synthesis , 1979 , 401 .
4.
Firouzabadi H.
,
Iranpoor N.
, and
Sobhani S.
, Tetrahedron Lett. , 2002 , 43 , 477 .
5.
Firouzabadi H.
,
Iranpoor N.
,
Sobhani S.
, and
Sardarian A.
, Tetrahedron Lett. , 2001 , 42 , 4369 .
6.
Sharghi H.
,
Niknam K.
, and
Massah A.R.
, J. Heterocycl. Chem. , 1999 , 36 , 601 .
7.
Shockravi A.
,
Sharghi H.
,
Valisadeh H.
, and
Heravi M.M.
, Phosphorus. Sulfur. Silicon. , 2002 , 177 , 2555 .
8.
Kazemi F.
,
Sharghi H.
, and
Nasseri M.A.
, Synthesis. , 2004 , 205 .
9.
Sarvari M.H.
, and
Sharghi H.J.
, J. Org. Chem. , 2004 , 69 , 6953 .
10.
Yadav J.S.
,
Reddy B.V.S.
,
Kondaji G.
,
Srinivasa R.R.
, and
Praveen K.S.
, Tetrahedron Lett. , 2002 , 43 , 8133 .
11.
Taylor J.E.
,
Jones M.D.
,
Williams J.M.J.
, and
Bull S.D.
, Org Lett. , 2010 , 24 , 5740 .
12.
Candy C.F.
,
Jones R.A.
, and
Wright P.H.
, J. Chem. Soc. , 1970 , 2563 .
13.
Kozikowski A.P.
, and
Ames A.
, J. Am. Chem. Soc. , 1980 , 102 , 860 .
14.
Nicolaou K.C.
,
Claremon D.A.
, and
Papahatjis D.P.
, Tetrahedron Lett. , 1981 , 22 , 4647 .
15.
Eyley S.C.
,
Giles R.G.
, and
Heaney H.
, Tetrahedron Lett. , 1985 , 26 , 4649 .
16.
Cornforth S.R.
, and
Huib D.M.
, J. Chem. Soc. Perkin. Trans., 1 , 1990 , 1463 .
17.
Katritzky A.R.
,
Suzuki K.
, and
Singh S.K.
, J. Org. Chem. , 2003 , 68 , 5720 .
18.
Song C.J.
,
Knight D.W.
, and
Whatton M.A.
, Tetrahedron Lett. , 2004 , 45 , 9573 .
19.
Tanaka K.
, and
Toda F.
, Chem. Rev. , 2000 , 100 , 1025 .
20.
Dharma G.B.
,
Kaushik M.P.
, and
Halve A.K.
, Tetrahedron Lett. , 2012 , 53 , 2741 .
21.
Mona H.S.
, and
Hashem S.
, Tetrahedron , 2005 , 61 , 10903 .
22.
Fatemeh T.
,
Mohammad A.A.
, and
Leily S.
, Tetrahedron Lett. , 2005 , 46 , 7841 .
23.
Barbero M.
,
Cadamuro S.
,
Degani L.
,
Fochi R.
,
Gatti A.
, and
Regondi V.
, J. Org. Chem. , 1988 , 53 , 2245 .
24.
Greenhouse R.
,
Ramirez C.
, and
Muchowski J.M.
, J. Org. Chem. , 1985 , 50 , 2961 .
25.
Anderson A.G.
, and
Exner M.M.
, J. Org. Chem. , 1977 , 42 , 3952 .
26.
Croce P.D.
,
Concetta L.R.
, and
Alberto R.
, Synthesis , 1989 , 783 .
27.
Su W.K.
,
Wu C.L.
, and
Su H.
, J. Chem. Res. , 2005 , 67 .