A method for electrochemical synthesis of 1h-indazole, 1h-indazole n-oxide and their derivatives

A novel electrochemical synthesis using a Zn or Pb cathode and RVC anode in a methanol-acetonitrile solvent system addresses the challenges of regioselective functionalization in 1H-indazole synthesis, achieving high-yield derivatives with functional groups at the C3 position without toxic precursors.

KR102994008B1Active Publication Date: 2026-07-21PUSAN NAT UNIV IND UNIV COOPERATION FOUND
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Patent Information

Authority / Receiving Office
KR · KR
Patent Type
Patents
Current Assignee / Owner
PUSAN NAT UNIV IND UNIV COOPERATION FOUND
Filing Date
2024-04-17
Publication Date
2026-07-21

AI Technical Summary

Technical Problem

Conventional methods for synthesizing 1H-indazole and 1H-indazole N-oxide face challenges in regioselective functionalization at the C3 position due to low reactivity and reigoselectivity, and existing electrochemical methods require toxic hydrazine or azide precursors.

Method used

A novel electrochemical synthesis method using a Zn or Pb cathode and RVC anode in a mixed solvent of methanol and acetonitrile with potassium acetate, allowing for the electrolysis of oximes to regioselectively introduce functional groups like carbon, oxygen, and sulfur at the C3 position of 1H-indazole derivatives.

Benefits of technology

The method enables high-yield synthesis of 1H-indazole and 1H-indazole N-oxide derivatives, facilitating the introduction of functional groups at the C3 position, overcoming the limitations of conventional methods and avoiding the use of toxic precursors.

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Abstract

The present invention discovers a novel synthesis method for 1H-indazole and 1H-indazole N-oxide that solves the limitations of conventional electrochemical synthesis, and by utilizing the 1H-indazole N-oxide synthesized through this method to regioselectively introduce functional groups such as carbon, oxygen, nitrogen, and sulfur at the C3 position, it is possible to effectively synthesize commercial pharmaceutical or physiologically active substances.
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