The rhodium(ii)-catalyzed one-pot three-component reaction of 3-diazooxindole, benzyl alcohol and isatin or ninhydrin or acenaphthenequinone was explored to synthesize 3-bisoxindoles, 2-oxindolyl-2-hydroxyindan-1,3-diones and 2-oxindolyl-2-hydroxyacenaphthylen-1-ones with vicinal stereo centres, respectively through oxonium ylides. Their antibacterial activities against Staphylococcus aureus NCIM 5021, Escherichia coli NCIM 2931, Pseudomonas aeruginosa NCIM 5029, Salmonella typhimurium NCIM 2501 and Proteus vulgaris NCIM 2813 were evaluated by a microdilution method. Group-based quantitative structure activity relationships (GQSAR) for all antibacterial activities were developed. The statistical measures namely r2 (0.66-0.85), r 2 adj (0.63-0.84), q2 (0.54-0.79) and F-ratio (11.63-34.17) were found to be satisfactory. All of the test and training set compounds were found to be within a 99% confidence level. Descriptors pertaining to hydrophobicity, topology and electrostatic interactions of the substitutions were found to contribute to their activities. © 2013 The Royal Society of Chemistry.