Structurally Divergent Reactivity of 2,2-Disubstituted Azetidines – Mechanistic Insights and Stereochemical Implications of Amide Coupling and Ring Expansion to 5,6-dihydro-4H-1,3-oxazines

Aditya K. Sahay; Callum S Begg; Xiurong Zhang; James A Bull; Alan C. Spivey

doi:10.1039/d5qo00804b

January 1, 2025Organic Chemistry FrontiersOpen Access

Structurally Divergent Reactivity of 2,2-Disubstituted Azetidines – Mechanistic Insights and Stereochemical Implications of Amide Coupling and Ring Expansion to 5,6-dihydro-4H-1,3-oxazines

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Key Points

The study uncovers divergent reactivity patterns in 2,2-disubstituted azetidines, impacting their application in drug development.
Key insights include the roles of amide coupling and ring expansion, which modify physiochemical properties crucial for biological activity.
The approach involves mechanistic investigations that highlight selective functionalization strategies for azetidines.
Understanding these reactions can enhance the design of conformationally constrained compounds in pharmaceuticals.

Implication

Observational analysis reveals the stereochemical implications of amide coupling and ring expansion in azetidine derivatives, suggesting potential for drug discovery.

Abstract

Azetidines have gained traction in drug discovery for their ability to introduce conformational constraint and modulate physiochemical properties. Strategies that enables their selective functionalization or controlled expansion into more complex...

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Cite This Study

Sahay et al. (2025) studied this question.

synapsesocial.com/papers/68bb3efd2b87ece8dc957ba5 https://doi.org/10.1039/d5qo00804b

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Structurally Divergent Reactivity of 2,2-Disubstituted Azetidines – Mechanistic Insights and Stereochemical Implications of Amide Coupling and Ring Expansion to 5,6-dihydro-4H-1,3-oxazines

Key Points

Implication

Abstract

Discussion

Cite This Study

Structurally Divergent Reactivity of 2,2-Disubstituted Azetidines – Mechanistic Insights and Stereochemical Implications of Amide Coupling and Ring Expansion to 5,6-dihydro-4H-1,3-oxazines

Key Points

Implication

Abstract

Discussion

Cite This Study

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