Abstract
Indoles (1a–e) react with cyclohexane-1,3-diones (2a–c) on montmorillonite K10 clay at 60–70 °C to furnish the corresponding 3-(3′-indolyl)cyclohex-2-en-1-ones (5a–e, 6a–e, 7b–e) in 27–75% yields in 2.5–4 h.
References
1.
Sundberg R.J.
, The Chemistry of Indoles , Academic Press , New York , 1970 .
2.
Remers W.A.
, in Indoles , Part 1, ed.
Houlihan W.J.
, Wiley-Interscience , New York , 1972 , pp. 1 –126 .
3.
Chakrabarty M.
,
Basak R.
, and
Harigaya Y.
, Heterocycles , 2001 , 55 , 2431 and references cited therein.
4.
Treibs A.
, and
Hermann E.
, Liebigs Ann. Chem. , 1954 , 589 , 207 .
5.
Banerji J.
,
Dhara K. P.
,
Saha M.
,
Das R.
,
Kanrar S.
,
Budzikiewicz H.
,
Neuman A.
, and
Prangé T.
, Ind. J. Chem. , 1994 , 33B , 949 .
6.
Banerji J.
,
Saha M.
,
Chakrabarti R.
,
Kanrar S.
,
Chaterjee A.
,
Budzikiewicz H.
,
Prangé T.
, and
Neuman A.
, J. Chem. Res. (S) , 1993 , 320 ; J. Chem. Res. (M) , 1993, 2201.
7.
Banerji J.
,
Saha M.
,
Kanrar S.
, and
Mukherjee P.
, Ind. J. Chem. , 1997 , 36B , 761 .
8.
Banerji J.
,
Chaterjee A.
,
Saha M.
,
Mukherjee P.
, and
Kanrar S.
, Ind. J. Chem. , 2003 , 42B , 2573 .
9.
Chakrabarty M.
,
Ghosh N.
,
Basak R.
, and
Harigaya Y.
, Tetrahedron Lett. , 2002 , 43 , 4075 .
10.
Chakrabarty M.
, and
Sarkar S.
, Tetrahedron Lett. , 2002 , 43 , 1351 .
11.
Brettle R.
,
Dunmur D. A.
,
Farrand L. D.
,
Hindley N. J.
, and
Marson C. M.
, Chem. Lett. , 1993 , 1663 .
12.
Bezborodov V.S.
,
Sanaouski G. M.
,
Lapanik V. I.
,
Debrowski R.
,
Dziaduszek J.
, and
Tyvoroskii V. I.
, Liq. Cryst. , 2001 , 28 , 1755 .
13.
Brettle R.
,
Dunmur D. A.
,
Farrand L. D.
, and
Marson C. M.
, J. Chem. Soc., Chem. Commun. , 1994 , 2305 .
14.
Marson C.M.
,
Farrand L. D.
,
Brettle R.
, and
Dunmur D. A.
, Tetrahedron , 2003 , 59 , 4377 .