Method of making 1,2-dioxetanes
The use of peroxomolybdate or peroxotungstate to react with enol ethers in a homogeneous liquid phase addresses the inefficiencies of existing 1,2-dioxetane synthesis, achieving high yield and purity with minimal side-products and cost-effective production.
WO2026125757A1 Publication Date: 2026-06-18BIOSYNTH
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Patent Information
- Application Number
- PCT/EP2025/086943
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-12-13
- Filing Date
- 2025-12-12
- Publication Date
- 2026-06-18
AI Technical Summary
Technical Problem
Existing synthesis methods for 1,2-dioxetanes suffer from low yield and purity, complex procedures, and the use of expensive equipment and chemicals, leading to undesirable side-products such as epoxides and ketones.
Method used
A method using peroxomolybdate or peroxotungstate to generate singlet oxygen, which reacts with enol ethers to form 1,2-dioxetanes under mild conditions, avoiding photoreactors and minimizing side-products, with reactions conducted in a homogeneous liquid phase using water-miscible protic solvents.
Benefits of technology
The method achieves high yield and purity of 1,2-dioxetanes with short reaction times, avoiding undesirable by-products and reducing the need for expensive equipment, while being easily monitored by NMR and HPLC.
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Abstract
The present invention relates to a method of making a 1,2-dioxetane by oxidizing an enol ether with a peroxomolybdate or peroxotungstate to give the 1,2-dioxetane. The method is particularly useful for making chemiluminescent 1,2-dioxetanes probes for use in a broad range of research and diagnostic applications, including the detection of pathogens and enzymes and chemiluminescent in vitro and in vivo imaging.
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