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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Solid-Phase Synthesis of s-Tetrazines.

Zainab S Alghamdi^1,2, Maxime Klausen¹, Alessia Gambardella¹

¹EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, U.K.

Organic Letters

|April 21, 2023

Summary

A new solid-phase synthesis efficiently produces s-tetrazines without harsh conditions. This method simplifies the creation of diverse tetrazines for bioorthogonal chemistry applications.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Classical tetrazine synthesis often yields mixtures and requires harsh conditions.
Solid-phase synthesis offers advantages in purification and reaction control.

Purpose of the Study:

To develop an efficient and versatile solid-phase synthesis for s-tetrazines.
To avoid metal catalysts and high temperatures in tetrazine preparation.

Main Methods:

Utilized thiol-promoted chemistry with dichloromethane for monosubstituted tetrazines.
Employed readily available nitriles for the synthesis of disubstituted unsymmetrical tetrazines.
Leveraged various solid-phase resins and linkers for compatibility.

Main Results:

Achieved high yields (70-94%) for synthesized s-tetrazines.
Successfully avoided the formation of symmetrical byproduct mixtures common in solution-phase methods.
Required only a single final purification step.

Conclusions:

The described solid-phase method provides an efficient route to diverse s-tetrazines.
This approach simplifies tetrazine synthesis, enabling rapid access for bioorthogonal chemistry.
The methodology is adaptable and avoids common limitations of traditional synthesis.