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Electro-Oxidative Synthesis of Phenazines.

Deepak Sharma1, Namrata Kotwal1, Pankaj Chauhan1

  • 1Department of Chemistry, Indian Institute of Technology Jammu, NH-44, Nagrota Bypass, Jammu 181221, J & K, India.

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Summary

Electro-oxidative synthesis provides a mild and efficient method for producing diverse phenazines. This protocol utilizes aerial oxygen and inexpensive materials, offering a versatile route to valuable chemical compounds.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • Phenazines are a significant class of nitrogen-containing heterocycles with diverse applications.
  • Traditional phenazine synthesis often involves harsh conditions or expensive reagents.
  • Developing milder and more sustainable synthetic routes is crucial.

Purpose of the Study:

  • To establish a general electro-oxidative protocol for phenazine synthesis.
  • To explore efficient methods for accessing various phenazine derivatives.
  • To utilize mild reaction conditions and readily available materials.

Main Methods:

  • Employing electro-oxidative synthesis using aerial oxygen as the oxidant.
  • Utilizing inexpensive electrolytes and electrodes.
  • Performing ring contraction of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines.
  • Investigating direct electro-oxidation of dihydrophenazines and electro-dimerization of o-phenylenediamines.

Main Results:

  • A diverse range of phenazines were synthesized in good yields.
  • The electro-oxidative protocol proved effective for ring contraction.
  • Successful synthesis of phenazines and diamino phenazines was achieved through alternative electro-oxidation pathways.

Conclusions:

  • Electro-oxidative synthesis offers a general, mild, and efficient method for phenazine procurement.
  • This approach provides a sustainable and cost-effective alternative to conventional methods.
  • The protocol is versatile, enabling access to various phenazine structures.