While N-(2-nitrobenzylidene)anilines produced mixtures of 2,1-benzisoxazoles and 3-anilino-2-aryl-2H-indazoles in the presence of indium and iodine in MeOH, N-(2-nitrobenzylidene)anilines were transformed into 3-anilino-2-aryl-2H-indazoles as the predominant major product through the change of the solvent from protic MeOH to aprotic THF. In an indium-mediated one-pot reductive reaction, 2-benzaldehydes and anilines in THF were also successfully transformed into the corresponding indazoles.
Indole derivatives R 0140Indium-HI-Mediated One-Pot Reaction of 1-(2-Arylethynyl)-2-nitroarenes to 2-Arylindoles. -Reductive cyclization of internal alkynes such as (I) is easily achieved in the presence of indium and aqueous HI. Indole formation fails in the presence of indium and catalytic amounts of InCl3, but the corresponding anilines are obtained in high yields. -(KIM, J. S.; HAN, J. H.; LEE, J. J.; JUN, Y. M.; LEE, B. M.; KIM*, B. H.; Tetrahedron Lett. 49 (2008) 23, 3733-3738; Dep. Chem., Kwangwoon Univ., Seoul 139-701, S. Korea; Eng.) -Mais 38-105
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