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One-pot synthesis of phenazines from 2-naphthols with 1, 2-diamines and its biological importance and binding studies

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Abstract

Synthesis of phenazine derivatives from the reaction of 2-naphthols with 1, 2-diamino benzenes in presence of K2S2O8 in AcOH and water, through the intermediate formation of 1, 2-naphthoquinones from self-coupling of 2-naphthol and then followed by condensation of 1, 2-diamino benzenes in one pot. The present reaction was compatible with various substituted 2-naphthols as well as substituted 1, 2-diamino benzenes to obtain a variety of substituted phenazine derivatives in good to excellent yields. The reaction was highly regio-selective in the case of unsymmetrical substituted 1, 2-diamino benzenes for providing single regio isomeric phenazine compounds. Reaction conditions were also mild and metal-free and also used green solvents such as AcOH and water. Phenazine derivatives are an important class of heterocycles and occur both in natural and synthetic compounds which shows many biological activities and also present in many important dyestuffs. In meantime, we have also shown our interest in antibacterial, anti-inflammatory activities and molecular docking studies. It is important to note that the phenazine derivatives showed excellent anti-bacterial and anti-inflammatory activities.

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Acknowledgements

Gajula Raju thanks UGC for providing BSR-SRF fellowship and BSN thanks DST-Purse for providing financial assistance to carry out research work and is also grateful to the Department of Chemistry, Osmania University Hyderabad, India for providing research facilities.

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Authors and Affiliations

  1. Department of Chemistry, University College of Science, Osmania University Campus, Hyderabad, 500 007, India

    Raju Gajula, Vijayacharan Guguloth & Satyanarayana Battu

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  1. Raju Gajula
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  2. Vijayacharan Guguloth
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  3. Satyanarayana Battu
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Correspondence to Satyanarayana Battu.

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Gajula, R., Guguloth, V. & Battu, S. One-pot synthesis of phenazines from 2-naphthols with 1, 2-diamines and its biological importance and binding studies. J Chem Sci 133, 49 (2021). https://doi.org/10.1007/s12039-021-01907-4

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  • DOI: https://doi.org/10.1007/s12039-021-01907-4

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