An efficient approach to the synthesis of fused pyrazole-annulated macrocycles has been demonstrated. Vilsmeier–Haack reaction of substituted o-hydroxyacetophenones with phenyl hydrazine followed by reduction of the resulting pyrazolyl aldehydes yielded the corresponding alcohols. These precursors upon alkylation with dibromoalkanes gave the target library. The structures of the synthesized products were established based on 1H, 13C NMR, IR, and mass spectral data. All the final macrocycles were screened for their antimicrobial activity. Compounds bearing electron-donating groups show promising antimicrobial activity against the tested strains.
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The authors are grateful to Department of Chemistry, Osmania University for providing laboratory facilities and the Central Facility for Research and Development, OU for providing spectral analysis. One of the authors, Mohan Gandhi Devulapally, is thankful to UGC-New Delhi for granting Senior Research Fellowship.
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Supplementary information file containing 1H and 13C NMR spectra is available at http://link.springer.com/journal/10593.
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(8), 609–614
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Ashok, D., Devulapally, M.G., Gundu, S. et al. Synthesis and Antimicrobial Evaluation of Novel Pyrazole-Annulated Oxygen-Containing Macrocycles. Chem Heterocycl Comp 52, 609–614 (2016). https://doi.org/10.1007/s10593-016-1939-y
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DOI: https://doi.org/10.1007/s10593-016-1939-y