Microwave irradiation (MWI) promotes the regioselective synthesis of 6H-indolo[2,3-b] quin oxaline (5) by condensation of isatin (1) with o-phenylenediamine. Ethyl indolo [2,3-b] quinoxaline-6-acetate (8) was prepared via the carbethoxymethylation of 5, or from the reaction of N-(ethoxycarbonylmethyl)isatin (6) with o-phenylenediamine under MWI. The reaction of 8 with hydrazine hydrate afforded the hydrazide 9, whose condensation with aromatic aldehydes and monosaccharides gave the hydrazones 10a–d.
MatsumotoT., WadaH., MigitaY., HatayamaK., and SekiguchiY., PCT Pat., 1994, 94 24, 135 (Chem. Abstr., 1995, 122, 160 684); J. Harmenberg, B. Wahren, J. Bergman, S. Akerfeldt and L. Lundblad, Antimicrob. Agents Chemother., 1988, 32, 1720; J. Harmenberg, A. Akesson-Johansson, A. Graslund, T. Malmfors, J. Bergman, B. Wakren, S. Akerfeldt, L. Lundblad and S. Cox, Antiviral Res., 1991, 15, 193; N. Patel, J. Bergman and A. Graslund, Eur. J. Biochem., 1991, 197, 597; G. Behravan, M. Leijon, U. Sehlstedt, B. Norden, H. Vallberg, J. Bergman and A. Graslund, Biopolymers, 1994, 34, 599; J. Bergman, C. Damberg and H. Vallberg, Recl. Trav. Chim. Pays-Bas, 1996, 115, 31.
2.
RashedN., Abdel HamidH., and El AshryE. S. H., Carbohydr. Res., 1993, 243, 399; A. Amer, A.M. El Massry, L. Awad, N. Rashed, E.S.H. El Ashry and D.M. Ho, J. Chem. Soc. Perkin Trans. 1, 1990, 2513; E.S.H. El Ashry, I.E. El Kholy and Y. El Kilany, Carbohydr. Res., 1978, 60, 303; E.S.H. El Ashry, I.E. El Kholy and Y. El Kilany, Carbohydr. Res., 1978, 60, 396; E.S. H. El Ashry, I.E. El Kholy and Y. El Kilany, Carbohydr. Res., 1978, 67, 495; E.S.H. El Ashry, H. Abdel Hamid and M. El Habrouk, Carbohydr. Res., 1995, 267, 177.
3.
Abdel-RahmanA.A. H., and El AshryE. S. H., Synlett., 2002, 2043.
4.
Abdel HamidH., RamadanE., HagarM., and El AshryE. S. H., Synth. Commun., 2004, 34, 377.
5.
El AshryE.S. H., RamadanE., Abdel HamidH., and HagarM., Synlett., 2004, 723.
6.
El AshryE.S. H., RamadanE., Abdel HamidH., and HagarM., Lett. Org. Chem., 2005, 2, 136.
7.
El AshryE.S. H., RamadanE., Abdel HamidH., and HagarM., Synth. Commun., 2005, 38, 1.
8.
El AshryE.S. H., RamadanE., KassemA. A., and HagarM., Adv. Heterocycl Chem., in press.
9.
LarhedM., MobergC., and HallbergA., Acc. Chem. Res., 2002, 35, 717; A. Lew, P.O. Krutzik, M.E. Hart and A.R. Chamberlin, J. Comb. Chem., 2002, 4, 95; C.O. Kappe, Curr. Opin. Chem. Biol., 2002, 6, 314; R.S. Varma, Tetrahedron, 2002, 58, 1235; H.E. Blackwell, Org. Biomol. Chem., 2003, 1, 1251; A.R. Katritzky and S.K. Singh, Arkivoc, 2003, xiii, 68: Y. Xu and Q.-X. Guo, Heterocycles, 2004, 63, 903.
10.
GedyeR.N., SmithF. E., and WestawayK. C., Can. J. Chem., 1988, 66, 17; D.M.P. Mingos and D.R. Baghurst, Chem. Soc. Rev., 1991, 20, 1; R.A. Abramovitch, Org. Prep. Proced. Intl., 1991, 23, 683; S. Caddick, Tetrahedron, 1995, 51, 10 403; R. Laurent, A. Laporterie, J. Dubac, J. Berlan, S. Lefeuver and M. Audhuy, J. Org. Chem., 1992, 57, 7099; D. Bogdal, J. Pielichowski and J. Jaskot, Org. Prep. Proc. Intl., 1998, 30, 427; A. Dandia, H. Sachdeva and R. Devi, J. Chem. Res. (S), 2000, 272; M. M. Mojtahedi, M. R. Saidi, M. M. Heravi and M. Bolourtchain, Monatsh. Chem., 1999, 130, 1175.
11.
SinghV.A., VarmaR. S., DwivediS. D., and VermaH. N., Indian Drugs, 1985, 22, 582; A.G. Drushlyak, A.V. Ivashchenko and V.V. Titov, Khim. Geterotsikl. Soedin, 1984, 1544 (Chem. Abstr., 1985, 102, 113425); K.D. Banerji, A.K.D. Mazumdar, K. Kumar and S.K. Guha, J. Indian Chem. Soc., 1979, 56, 396; T.S. Hafez, Phosphorus, Sulfur Silicon, 1991, 61, 341; K. Niume, F. Toda, K. Uno, M. Hasegawa and Y. Iwakura, J. Polymer Sci. Polymer Chem. Ed., 1983, 21, 615; F.D. Popp, J. Heterocycl. Chem., 1969, 6, 125; F.D. Popp, J. Heterocycl. Chem., 1972, 9, 1399; G. Henseke and W. Lemke, Chem. Ber., 1958, 91, 101.
