2-Hydroxy-2,2′-biindan-1,1′,3,3′-tetrone 1 upon stirring with moderately activated and deactivated arenes in superacidic triflic acid (CF3SO3H, TfOH) medium produces arylated adducts 2-aryl-2,2′-biindan-1,1′,3,3′-tetrones 3 within 1-2 h. Prolonged stirring (12–24 h) of the same reaction mixture gives rearranged products 3-(aryl-1,3-indanedionylmethylene)isobenzofuranones 4 involving three types of regioselectivity. The arylated adducts 3 and rearranged products 4 undergo nucleophilic ring opening and condensation with hydrazine hydrate to produce 4-substituted mono- and diphthalazinones depending upon the reaction temperature.
YamaguchiM., KameiK., KogaT., AkimaM., KurokiT., and OhiN., J. Med. Chem., 1993, 36, 4052.
9.
(a) MarcacciniS., PepinoR., PoloC., and PozoM.C., Synthesis, 2001, 85; (b) J. Epsztajn, Z. Malinowski, J.Z. Brzezinki and M. Karzatka, Synthesis, 2001, 2085; (c) Y. Saito, T. Sakamoto and Y. Kikugawa, Synthesis, 2001, 221; (d) A.M. Bernard, M.T. Cocco, C. Congiu, V. Onnis and P.P. Piras, Synthesis, 1998, 317; (e) N.R. Patel, Condensed Pyridazines Including Cinnolines and Phthalazines; CastleR.N., Ed.; Wiley-Interscience: New York, 1973, 383; (f) M. Yamaguchi, K. Kamei, T. Koga, M. Akima, A. Maruyama, T. Kuroki and N. Ohi, J. Med. Chem., 1993, 36, 4061; (g) S.K. Kundu, A. Pramanik and A. Patra, Synlett, 2002, 823; (h) S. Das, R. Fröhlich and A. Pramanik, J. Chem. Res., 2006, 84; (i) M. Pal, V.R. Batchu, K. Parasuraman and K.R. Yeleswarapu, J. Org. Chem., 2003, 68, 6806.
10.
Data sets were collected with Nonius KappaCCD diffractometers, in case of Mo-radiation equipped with a rotating anode generator. Programs used: data collection COLLECT (B.V. Nonius, 1998), data reduction Denzo-SMN (Z. Otwinowski and W. Minor, Methods in Enzymology, 1997, 276, 307), structure solution SHELXS-97 (G.M. Sheldrick, Acta Cryst., 1990, A46, 467), structure refinement SHELXL-97 (G.M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997).
