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Synthesis
DOI: 10.1055/a-2746-2513
Paper

PIDA-Mediated Synthesis of Symmetrical 1,2,4,5-Tetrazine Using N-Tosylhydrazones

Authors

  • Rakshanda Singhal

    1   School of Physical and Biological Sciences, Department of Chemistry, Manipal University Jaipur, Jaipur, India

  • Manish Kumar Mehra

    2   Department of Chemistry, Gachon University, Seongnam, Gyeonggi, Republic of Korea

  • Babita Malik

    1   School of Physical and Biological Sciences, Department of Chemistry, Manipal University Jaipur, Jaipur, India

  • Meenakshi Pilania 

    1   School of Physical and Biological Sciences, Department of Chemistry, Manipal University Jaipur, Jaipur, India
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Graphical Abstract

Abstract

A rapid and effective method for the preparation of 3,6-disubstituted-1,2,4,5-tetrazines from N-tosylhydrazones has been developed using phenyliodine(III) diacetate as an oxidant and cesium carbonate (Cs₂CO₃) as a base. The reaction completes in a single step under transition-metal-free conditions through an oxidative C–N bond-formation approach. This developed method offers numerous advantages, including a short reaction time (15 min), operational simplicity, mild conditions, and moderate to high product yields. In general, this methodology offers a practical and useful approach for synthesizing 1,2,4,5-tetrazine scaffolds, which are highly valuable in both synthetic and medicinal chemistry.

Keywords

N-Tosylhydrazone - Hypervalent iodine - Phenyliodine(III) diacetate - 1,2,4,5-Tetrazine - Aromatization

Supplementary Material



Publication History

Received: 24 September 2025

Accepted after revision: 12 November 2025

Article published online:
09 December 2025

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