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.532 534 Under slightly different conditions,N-alkylformanilides and POCl3 yield the indolo[3,2-b]quinol-12.1 Oxidation of indolinesines (Scheme 133).534Although indolines (2,3-dihydroindoles) are an obvious vehiclefor the synthesis of indoles, there has never been an efficient,general method for this oxidation reaction.However, a few newmethods to address this problem have been described in recentyears.The use of catalytic tetra-n-propylammonium perruthenatein the presence of N-methylmorpholine N-oxide is reported byGoti and Romani to oxidize indoline to indole in 73% yield.518The generality of this conversion remains to be seen.CarterScheme 132and Van Vranken have observed the photooxidation of 2-indol-2-ylindolines to 2,2 -biindolyls,519 and Giethlen and Schaushave investigated the mechanism of the oxidation of indolineswith potassium nitrosodisulfonate (Frémy s salt) to furnisheither indoles or 5-hydroxyindoles.520 It was determined by isol-ation that an intermediate iminoquinone forms in this reaction.Ketcha et al.have utilized Mn(iii) in the oxidation of 2-methyl-1-(phenylsulfonyl)indolines to the corresponding 2-acetoxy-methylindoles (Scheme 131).521Scheme 133An unusual cyanide-induced skeletal rearrangement of 3-acyl- and 3-ethoxycarbonyl-1,2-dihydrocinnoline-1,2-dicarbox-imides leads to 2-acyl- and 2-ethoxycarbonyl-3-cyanoindoles(Scheme 134),535 a reaction based on similar rearrangementsdiscovered earlier.536 538Scheme 13112.2 From oxindoles, isatins and indoxylsSince we have included in this review the synthesis of oxindoles,isatins, and indoxyls, it seems appropriate to cite newer methodsand applications for the conversion of these compounds toindoles.Williams and co-workers have employed the combination ofNaBH4 and BF3 OEt2 to reduce an oxindole to an indole intheir synthesis of ( )-paraherquamide B.206 Other reductionScheme 134methods were unsuccessful.Black and Rezaie have coupledoxindoles with benzofurans using triflic anhydride to give 2- Ciufolini et al.have used the cyclization of 2-amino-2,3-indolylbenzofurans,522 and Beccalli and Marchesini have syn- dihydrobenzoquinone monoketals to obtain fused indolinesthesized 3-acyl-2-vinylindoles from chloroalkylidene oxindoles after appropriate manipulation.539 Studies by Paz and Hopkins1068 J.Chem.Soc., Perkin Trans.1, 2000, 1045 1075on the antitumor antibiotic agents FR66979, FR900482, and 14 ReferencesFK973, which are DNA crosslinkers similar to mitomycin C,1 G.W.Gribble, Contemp.Org.Synth., 1994, 145.indicate that cyclization to an indole is likely involved in the2 The reader is also referred to these other reviews (a) U.Pindur andmode of action of these compounds.540 Rigby and co-workersR.Adam, J.Heterocycl.Chem., 1988, 25, 1; (b) C.J.Moody, Synlett,have developed several variations of the reaction between vinyl 1994, 681; (c) R.J.Sundberg, Indoles, Academic Press, San Diego,CA, 1996; (d ) T.L.Gilchrist, J.Chem.Soc., Perkin Trans.1, 1999,isocyanates and isocyanides or nucleophilic carbenes to afford2848.functionalized oxindoles or isatins.Thus, these workers have3 B.Robinson, The Fischer Indole Synthesis, Wiley-Interscience,prepared simple hydrooxindoles,541 543 oxindoles (SchemeNew York, 1982.135),544 hydroisatins,545 546 and the alkaloid degradation product4 D.L.Hughes, Org.Prep.Proced.Int., 1993, 25, 607.(±)-±-lycorane.5475 V.Sridar, Indian J.Chem., Sect.B, 1996, 35, 737.6 V.Sridar, Indian J.Chem., Sect.B, 1997, 36, 86.7 J.An, L.Bagnell, T.Cablewski, C.R.Strauss and R.W.Trainor,J.Org.Chem., 1997, 62, 2505.8 T.Lipinska, E.Guibé-Jampel, A.Petit and A.Loupy, Synth.Commun., 1999, 29, 1349.9 G.Penieres, R.Miranda, J.García, J.Aceves and F.Delgado,Heterocycl.Commun., 1996, 2, 401.10 M.S.Rigutto, H.J.A.de Vries, S.R.Magill, A.J.Hoefnagel andH.van Bekkum, Stud.Surf.Sci.Catal., 1993, 78, 661.11 P.J.Kunkeler, M.S.Rigutto, R.S.Downing, H.J.A.de Vries andH.van Bekkum, Stud.Surf.Sci.Catal., 1997, 105B, 1269.12 Y.Cheng and K.T.Chapman, Tetrahedron Lett., 1997, 38, 1497.13 S.M.Hutchins and K.T.Chapman, Tetrahedron Lett., 1996, 37,4869.Scheme 13514 R.M.Kim, M.Manna, S.M.Hutchins, P.R.Griffin, N.A.Yates,A.M.Bernick and K.T.Chapman, Proc.Natl.Acad.Sci.USA,An unusually facile cyclization of tetrahydroisoquinoline 641996, 93, 10012.leads to the indolo[2,1-a]isoquinoline ring system (Scheme 15 O.Miyata, Y.Kimura, K.Muroya, H.Hiramatsu and T.Naito,Tetrahedron Lett., 1999, 40, 3601.136).548 Several examples of this reaction were reported.16 K.Maruoka, M.Oishi and H.Yamamoto, J.Org.Chem., 1993, 58,7638.17 (a) S.Wagaw, B.H.Yang and S.L.Buchwald, J.Am.Chem.Soc.,1998, 120, 6621; 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