A convenient ultrasound assisted synthesis of new anti-bacterialhydrazines from methyl anthranilate is reported. Methyl anthranilate was reacted with methane sulfonyl chloride, followed by N-alkylation and subsequent base catalyzed cyclization. Hydrazinolysis of the cyclized products followed by their ultrasound mediated condensations with different benzaldehydes yielded the title compounds. Some of these compounds showed good anti-bacterial activity against Pseudomonas aeruginosa, Salmonella typhimurium and Staphylococcus aureus.
Quinacridone diimines 1-10 were synthesized by the condensation of anilines with alkyl substituted quinacridones (QA). Photophysical and electrochemical properties of the compounds were investigated. Unconventional behavior of absorption spectra suggested a decrease in p _ conjugation within the QA skeleton as well as lack of extended p _ conjugation between the QA skeleton and the N-phenyl rings. A computational study of compounds 1-10, a variable temperature 1 H NMR study of compounds 2, 7 and 10 (for instance), and single crystal X-ray analysis of 2, 3, 6, 7, 8 and 10 indicated that the anomalous behavior is due to the buckled, non-planar structure of the quinacridones. Moreover the molecules existed in two interconvertible geometric isomeric forms at different temperatures. Molecular orbital calculations were performed at B3LYP/6-31+G(d), B3PW91/6-31G(d) and PBEPBE/6-31G(d) levels of theory at B3PW91/6-31G(d) optimized structures for both isomers of all compounds (1-10); the results obtained are in close agreement with the experimentally determined values.
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