Reductive heterocyclizations via indium-iodine-promoted conversion of 2-nitroaryl imines or 2-nitroarenes to 2,3-diaryl-substituted indazoles.
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.
Ahn
Gil Hwan
GH
Department of Chemistry, Kwangwoon University, Seoul 139-701, Korea.
Lee
Jung June
JJ
Jun
Young Moo
YM
Lee
Byung Min
BM
Kim
Byeong Hyo
BH
D000814:Aniline Compounds / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007191:Indazoles / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010084:Oxidation-Reduction
D000814:Aniline Compounds; D001547:Benzaldehydes; D007097:Imines; D007191:Indazoles; D007204:Indium; C043850:2-nitrobenzaldehyde; D007455:Iodine; D009584:Nitrogen; C023650:aniline