Abstract
The ring contraction of N-acetyl-2-aryl-1,2,3,4-tetrahydro-4-quinolones with [hydroxy(tosyloxy)iodo]benzene to trans methyl N-acetyl-2-aryl-2,3-dihydroindol-3-carboxylates in trimethylorthoformate in good yield is described.
References
1.
(a)
Stang P.J.
, and
Zhdankin V. V.
, Chem. Rev. , 2002 , 102 , 2523 ; (b) R.M. Moriarty, J. Org. Chem. , 2005, 70 , 2893; (c) T. Worth, Angew. Chem. Int. Ed. , 2005, 44 , 3656; (d) L.F. Silva, Jr, Molecules , 2006, 11 , 421; (e) G.F. Koser, Adv. Heterocycl. Chem. , 2004, 86 , 225.
2.
Prakash O.
,
Kumar D.
,
Saini R.K.
, and
Singh S.P.
, Synth. Commun. , 1994 , 24 , 2167 .
3.
Varma R.S.
, and
Kumar D.
, Tetrahedron Lett. , 1998 , 39 , 9113 .
4.
Mphahlele M.J.
,
Mogamisi F.K.
,
Tsanwani M.
,
Hlatshwayo S.M.
, and
Mampa K.M.
, J. Chem. Res. (S) , 1999 , 706 .
5.
Prakash O.
,
Kumar D.
,
Saini R.K.
, and
Singh S.P.
, Tetrahedron Lett. , 1994 , 35 , 4211 .
6.
Nasser A.M.
, and
Court W.E.
, J. Ethanopharmacol. , 1984 , 11 , 99 .
7.
Buchi G.
, and
Kamikawa T.
, J. Org. Chem. , 1977 , 42 , 4153 .
8.
Florvall L.
,
Kumar Y.
,
Ask A.L.
,
Fagervall I.
,
Renyi L.
, and
Ross S.B.
, J. Med. Chem. , 1986 , 29 , 1406 .
9.
Dhanoa D.S.
,
Bagley S.W.
,
Chang R.S.L.
,
Lotti V.J.
,
Chen T.B.
,
Kivlighn S.D.
,
Zingaro G.J.
,
Siegl P.K.S.
,
Patchett A.A.
, and
Greenlee W.J.
, J. Med. Chem. , 1993 , 36 , 4230 .
10.
(a)
Witulski B.
, and
Stengel T.
, Angew. Chem. Int. Ed. , 1999 , 38 , 2426 ; (b) W.H. Cheung, S.L. Zheng, W.Y. Yu, G.C. Zhou and C.M. Che, Org. Lett. , 2003, 5 , 2535; (c) M. Beller, C. Breindl, T.H. Riermeler and A. Tillack, J. Org. Chem. , 2001, 66 , 1403; (d) G.W. Gribble, J. Chem. Soc. Perkin Trans. 1 , 2000, 1045; (e) D.P. Curran, C.H.T. Chen, S.J. Geib and A.J.B. Lapierre, Tetrahedron , 2004, 60 , 4413.
11.Aldrich Chemical Catalogue , 2007 .
12.
McComas C.C.
,
Gilbert E.J.
, and
Vranken V.
, J. Org. Chem. , 1997 , 62 , 8600 .
13.
Engler T.A.
,
Chai W.
, and
LaTessa K.O.
, J. Org. Chem. , 1996 , 61 , 9297 .
14.
Singh O.V.
,
Muthukrishnan M.
, and
Sundaravdvelu M.
, Synth. Commun. , 2006 , 36 , 943 .
15.
Patonay T.
,
Levai A.
,
Riman E.
, and
Varma R.S.
, Arkivoc , 2004 , (vii), 183 .
16.
Donnelly J.A.
, and
Farrel D.F.
, J. Org. Chem. , 1990 , 55 , 1757 ; Tetrahedron , 1990, 46 , 885.