Abstract
Potassium aluminum sulfate (Alum) efficiently catalyses the electrophilic substitution reaction of indole and isatin in aqueous solution at room temperature and under microwave irradiation to afford the new corresponding bis(indol-3-yl)methanes (DIM) and the new corresponding oxindoles.
References
1.
(a)
Azizian J.
,
Varasteh Morady A.
,
Soozangarzadeh S.
, and
Asadi A.
, Tetrahedron Lett. , 2002 , 43 , 9721 .
2.
Azizian J.
, and
Mehrdad M.
, Tetrahedron Lett. , 2000 , 14 , 5265 .
3.
Azizian J.
, and
Jadidi K.
, Synth. Commun. , 2000 , 30 , 2309 .
4.
Azizian J.
, and
Sarrafi Y.
, Indian J Chem. , 2000 , 39B , 304 .
5.
Azizian J.
,
Karimi Ali R.
, and
Mohammadi Ali A.
, Synth. Commun. , 2003 , 33 , 383 .
6.
Azizian J.
,
Mohammadi Ali A.
,
Ardakani F.
,
Karimi Ali R.
, and
Mohammadizadeh M. R.
, Heterocycles (in press).
7.
(a)
McDougal A.
,
Gupta M. S.
,
Ramamoorthy K.
,
Sun G.
, and
Safe S. H.
, Cancer Lett. , 2000 , 151 , 169 .
8.
Chen I.
,
Mc Dougal A.
,
Wang F.
, and
Safe S.
, Carcinogenesis , 1998 , 19 , 1631 .
9.
Dzvinchuk I.B.
,
Makitruk T. V.
, and
Lozinskii M. O.
, Khimiya Geterotsiklicheskikh Soedinell , 2002 , 8 , 1141 .
10.
Chang Y.C.
,
Riby J.
,
Chang G. H. F.
,
Peng B. C.
,
Firestone G.
, and
Bjeldanes L. F.
, Biochem. Pharmacol. , 1999 , 58 , 825 .
11.
Hong C.B.
,
Kim H. A.
,
Firestone G. L.
, and
Bjeldanes L. F.
, Carcinogenesis , 2002 , 23 , 1297 .
12.
Chen D.Z.
,
Qi M.
,
Auborn K. J.
, and
Carter T. H.
, J. Nutr. , 2001 , 131 , 3294 .
13.
(a)
Chen I.
,
Safe S.
, and
Bjeldanes L.
, Biochem. Pharmacol. , 1996 , 51 , 1069 .
14.
Hong C.
,
Firestone G. L.
, and
Bjeidanes L. F.
, Biochemical Pharmacology , 2002 , 63 , 1085 .
15.
(a)
Popp F.D.
, J. Heterocyclic. Chem. , 1984 , 21 , 1367 .
16.
Pajouhesh H.
,
Parsons R.
, and
Popp F. D.
, J. Pharm. Sci. , 1983 , 72 , 318 .
17.
Garrido F.
,
Ibanez J.
,
Gonalons E.
, and
Giraldez A.
, Eur. J. Med. Chem. , 1975 , 10 , 143 .
18.
(a)
Maiti A.M.
, and
Bhattacharyya P.
, J. Chem. Research (S)., 1997 , 424 .
19.
Gregorovih B.
,
Liang K.
,
Clugston D.
, and
Macdonald S.
, Canad. J. Chem. , 1968 , 46 , 3291 .
20.
(a)
Room M.
, and
Macdonald S.
Can. J. Chem. , 1970 , 48 , 139 .
21.
Kmala A.
, and
Qureshi Ali A.
, Tetrahedron , 1963 , 19 , 513 .
22.
(a)
Noland W.
,
Venkites Waren M.
, and
Richards C.
, J. Org. Chem. , 1961 , 26 , 4241 .
23.
Chatterjee A.
,
Manna S.
,
Benerji J.
,
Pascard C.
,
Prange T.
, and
Shoolery J.
, J. Chem. Soc. Perkin Trans. I ., 1980 , 553 .
24.
Chen D.
,
Yu L.
, and
Wang P. G.
, Tetrahedron Lett. , 1995 , 36 , 4467 .
25.
Banerji J.
,
Dutta U.
,
Basak B.
,
Saha M.
,
Budzikiewicz H.
, and
Chatterjee A.
, Indian. J. Chem. Sect. B-Org. Chem. Med. Chem. , 2001 , 40 , 981 .
26.
Klumpp A.D.
,
Yeung K.
,
Surya Prakash G. K.
, and
Olah G. A.
, J. Org. Chem. , 1998 , 63 , 4481 .
27.
Franklin D.P.
, Ger. Patent 1973 , 2258505 .
28.
Jursic B.
, and
Stevens E. D.
, Tetrahedron Lett. , 2002 , 43 , 5681 .
29.
(a)
Seno M.
,
Shiraishi S.
,
Suzuki Y.
, and
Asahara T.
, Bull. Chem. Soc. Jpn. , 1978 , 51 , 1413 .
30.
Sarel S.
,
Klug J.
,
Breaer E.
, and
Angel F. D.
, Tetrahedron Lett. , 1964 , 5 , 1553 .
31.
Witkop B.
, and
Arvid E. K.
, J. Am. Chem. Soc. , 1951 , 73 , 5664 .
32.
De Silva J.F. M.
,
Garden S. J.
, and
Pinto A. C. J.
, Braz. Chem. Soc. , 2001 , 12 , 273 .
33.
Zhungietu G.I.
, and
Sinyavskaya L. P.
, Khim. Get. Soedin. , 1976 , 204 .
34.
For reviews on microwave assisted organic reaction see: (a)
Loupy A.
,
Petit A.
,
Hamelin J.
,
Texier-Boullet F.
,
Jacquault P.
, and
Mathe D.
, Synthesis. , 1988 , 1213 .
35.
Lidstrom P.
,
Tierney J.
,
Wathey B.
, and
Westman J.
, Tetrahedron , 2001 , 57 , 9225 .
36.
Bergman J.
, and
Eklund N.
, Tetrahedron , 1980 , 36 , 1445 .
