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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...

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Elucidation of the Material Basis of Yiqi Qingjie Formula Against IgA Nephropathy Using UHPLC-Q-Orbitrap HRMS Integrated with Network Pharmacology
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A hydrogen peroxide based access to qinghaosu (artemisinin).

Hong-Dong Hao1, Yun Li, Wei-Bo Han

  • 1State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Organic Letters
|July 19, 2011
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Summary

A novel molybdenum catalyst facilitates the attachment of hydrogen peroxide (H2O2) to a key artemisinin precursor. This breakthrough offers a new, simpler synthetic route to artemisinin, a vital malaria treatment.

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Optimized Griess Reaction for UV-Vis and Naked-eye Determination of Anti-malarial Primaquine
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Optimized Griess Reaction for UV-Vis and Naked-eye Determination of Anti-malarial Primaquine
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Optimized Griess Reaction for UV-Vis and Naked-eye Determination of Anti-malarial Primaquine

Published on: October 11, 2019

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Artemisinin (qinghaosu) is a crucial drug for malaria treatment.
  • Existing synthetic routes to artemisinin are often complex and lengthy.
  • Development of efficient and novel synthetic pathways is essential.

Purpose of the Study:

  • To develop a facile and efficient method for synthesizing artemisinin precursors.
  • To introduce a new synthetic strategy for incorporating key functional groups.
  • To explore the utility of a novel molybdenum catalyst in organic synthesis.

Main Methods:

  • Perhydrolysis of a spiro epoxy ring in an artemisinin precursor.
  • Utilized a previously unknown molybdenum species as a catalyst.
  • Reaction performed without specialized equipment or complex procedures.

Main Results:

  • Successfully achieved the attachment of hydrogen peroxide (H2O2) to the highly hindered quaternary C-12a position.
  • Generated a β-hydroxyhydroperoxide intermediate.
  • Demonstrated the feasibility of further elaboration into artemisinin.

Conclusions:

  • A novel and simplified synthetic route to artemisinin has been established.
  • The new method offers a fundamentally different approach compared to existing syntheses.
  • This advancement holds significant potential for the production of malaria chemotherapy agents.