Abstract
A variety of enamines are easily and efficiently synthesised in short reaction times and moderate to high yields from corresponding acyclic and cyclic ketones using sulfuric acid–silica catalyst.
References
1.
(a)
Heyl F.W.
, and
Herr M. E.
, J. Am. Chem. Soc. , 1953 , 75 , 1918 .
2.
Herr M.E.
, and
Heyl F. W.
, J. Am. Chem. Soc. , 1953 , 75 , 5927 .
3.
Roberts J.D.
, Org. Synth. , 1961 , 41 , 65 .
4.
Mondon A.
, Chem. Ber. , 1959 , 92 , 1461 .
5.
Hunig S.
,
Benzin E.
, and
Lucke E.
, Chem. Ber. , 1957 , 90 , 2833 .
6.
Semmelhack M.F.
, Org. Synth. , 1984 , 62 , 191 .
7.
Jacquir R.
,
Petrus C.
, and
Petrs F.
, Bull. Soc. Chim. France. , 1966 , 2845 .
8.
Johnson J.L.
,
Herr M. E.
,
Babcock J. C.
,
Fonken A. E.
,
Stafford J. E.
, and
Heyl F. W.
, J. Am. Chem. Soc. , 1956 , 78 , 430 .
9.
Zoretic P.A.
,
Barcelos F.
, and
Branchaud B.
, Org. Prep. Proc. Int. , 1976 , 8 , 211 .
10.
Ansell M.F.
,
Mason J. S.
, and
Caton M. P. L.
, J. Chem. Soc., Perkin Trans., 1 , 1984 , 1061 .
11.
Taguchi K.
, and WF. H., J. Org. Chem. , 1971 , 36 , 1570 .
12.
(a)
Graham Solomons T.W.
, Organic Chemistry , Chap. 20, pp. 913 –915 , 1992 , 5th edn.
13.
Stork G.
,
Brizzolara A.
,
Landesman H.
,
Szmuszkovicz J.
, and
Terrell R.
, J. Am. Chem. Soc. , 1963 , 85 , 207 .
14.
Heyl F.W.
, and
Herr M. E.
, J. Am. Chem. Soc. , 1955 , 77 , 488 .
15.
White W.A.
, and
Weingarten H.
, J. Org. Chem. , 1967 , 32 , 213 .
16.
Weingarten H.
, and
White W. A.
, J. Org. Chem. , 1966 , 31 , 4041 .
17.
Von Hirsch H.
, Chem. Ber. , 1967 , 100 , 1289 .
18.
Pommier J.C.
, and
Roubineau A.
, J. Organomet. Chem. , 1973 , 50 , 101 .
19.
Nelson P.
, and
Pelter A.
, J. Chem. Soc. , 1966 , 4041 .
20.
Koketsu J.
, and
Ishii Y.
J. Chem. Soc. , 1971 , 511 .
21.
Ando F.
,
Ohashi K.
, and
Koketsu A.
, J. Bull. Chem. Soc. Jpn. , 1976 , 47 , 727 .
22.
Clark J.H.
, Catalysis of Organic Reactions by Supported Inorganic Reagents , 1996 .
23.
(a)
Tanaka K.
, and
Toda F.
, Chem. Rev. , 2000 , 100 , 1025 and references cited therein.
24.
Varma R.S.
, Green Chem. , 1999 , 1 , 43 and references cited therein.
25.
Toda F.
, Acc. Chem. Res. , 1995 , 28 , 480 .
26.
Stuerga D.
, and
Gaillard P.
, Tetrahedron , 1996 , 52 , 5505 .
27.
(a)
Alavi Nikje M.M.
, and
Bigdeli M. A.
, Phosphorus, Sulfur and Silicon , 2004 , 179 , 1445 .
28.
Alavi Nikje M.M.
,
Bigdeli M. A.
, and
Imanieh H.
, Phosphorus, Sulfur and Silicon. , 2004 , 179 , 1465 .
29.
Alavi Nikje M.M.
,
Bigdeli M. A.
, and
Heravi Majid M.
, Phosphorus, Sulfur and Silicon. , 2002 , 177 , 15 .
30.
Bigdeli M.A.
,
Alavi Nikje M. M.
, and
Heravi Majid M.
, Phosphorus, Sulfur and Silicon , 2002 , 177 , 2309 .
31.
Bigdeli M.A.
, and
Alavi Nikje M. M.
, Monats. Chemi. , 2001 , 132 , 1547 .
32.
Bigdeli M.A.
,
Alavi M. M.
,
Jafari N. S.
, and
Heravi M. M.
, J. Chem. Res.(S). , 2001 , 20 .
33.
Bigdeli M.A.
,
Alavi Nikje M. M.
, and
Heravi Majid M.
, J. Chem. Res.(S.) , 2001 , 496 .
