2-Azadiene-Derived 2-Amino-2 H -1,4-oxazines as Intermediates on the Way to 2,3-Fused Pyrrolo[3,4- d ]oxazoles

Anastasiya V. Agafonova; Pavel O. Kuliaev; Ilia A. Smetanin; Alexander F. Khlebnikov; Михаил С. Новиков

doi:10.1021/acs.orglett.6c02605

July 26, 2026Organic Letters

2-Azadiene-Derived 2-Amino-2 H -1,4-oxazines as Intermediates on the Way to 2,3-Fused Pyrrolo[3,4- d ]oxazoles

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Key Points

The aim is to explore the novel reactivity of 2-azadienes, leading to the discovery of azomethine ylides through a multi-step transformation.
Utilized a retroelectrocyclization/1,6-prototropy/intramolecular 1,3-dipolar cycloaddition cascade for the transformation.
Analyzed the formation of intermediates and final products during the reaction process.
Demonstrated a previously unknown mode of reactivity for 2-azadienes.
Successfully generated azomethine ylides for the first time through prototropy.

Implication

This research finds new 2-azadiene reactivity producing azomethine ylides, revealing an innovative transformation method.

Abstract

]oxazoles through a retroelectrocyclization/1,6-prototropy/intramolecular 1,3-dipolar cycloaddition cascade. This transformation reveals a previously unknown mode of 2-azadiene reactivity and demonstrates, for the first time, the generation of azomethine ylides from 2-azadienes by prototropy.

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Cite This Study

Agafonova et al. (2026) studied this question.

synapsesocial.com/papers/6a69a28ac8da07d9defa6070 https://doi.org/10.1021/acs.orglett.6c02605

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2-Azadiene-Derived 2-Amino-2 H -1,4-oxazines as Intermediates on the Way to 2,3-Fused Pyrrolo[3,4- d ]oxazoles

Key Points

Implication

Abstract

Discussion

Cite This Study

2-Azadiene-Derived 2-Amino-2 H -1,4-oxazines as Intermediates on the Way to 2,3-Fused Pyrrolo[3,4- d ]oxazoles

Key Points

Implication

Abstract

Discussion

Cite This Study

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