Practical and Scalable Entry to Halogenated 1,4-Thiazines Through a Domino Morin-Rearrangement/Halogenation of N,S-Acetals and their Arylation Based on Suzuki-Miyaura Coupling

Fanny Danton; Kouceila Abdelli; Mohamed O. Othman; Ata Martin Lawson; Hassan Oulyadi; Sergiu Shova; Ján Moncóľ; Alina Ghinet; Adam Daı̈ch

doi:10.1039/d6ob00454g

January 1, 2025Organic & Biomolecular Chemistry

Practical and Scalable Entry to Halogenated 1,4-Thiazines Through a Domino Morin-Rearrangement/Halogenation of N,S-Acetals and their Arylation Based on Suzuki-Miyaura Coupling

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Key Points

To develop a practical and scalable method for synthesizing halogenated thiazines.
Utilized Morin-rearrangement of N,S-acetals.
Conducted halogenation to introduce halides at the α-position of thiazines.
Employed Suzuki-Miyaura coupling for arylation.
Successfully synthesized thiazines with halides at α-position.
Demonstrated one or two-step synthesis efficiency without extensive conditions.
Provided a new scalable route that could enhance future applications in organic synthesis.

Implication

Demonstrates halogenated thiazines production in a scalable way, suggesting a new synthesis method.

Abstract

Thiazines frameworks bearing a halide X (X = I, Br or Cl) at α-position of their sulfur atom were prepared in one or twosteps. The approach consists on Morin-rearrangement of...

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Cite This Study

Danton et al. (2025) studied this question.

synapsesocial.com/papers/69fd7eb0bfa21ec5bbf06f75 https://doi.org/10.1039/d6ob00454g

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Practical and Scalable Entry to Halogenated 1,4-Thiazines Through a Domino Morin-Rearrangement/Halogenation of N,S-Acetals and their Arylation Based on Suzuki-Miyaura Coupling

Key Points

Implication

Abstract

Discussion

Cite This Study

Practical and Scalable Entry to Halogenated 1,4-Thiazines Through a Domino Morin-Rearrangement/Halogenation of N,S-Acetals and their Arylation Based on Suzuki-Miyaura Coupling

Key Points

Implication

Abstract

Discussion

Cite This Study

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