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

]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.

Authors

Alexander F. Khlebnikov (ORCID: https://orcid.org/0000-0002-6100-0309)
Pavel O. Kuliaev
Anastasiya V. Agafonova (ORCID: https://orcid.org/0000-0003-1855-7440)
Ilia A. Smetanin (ORCID: https://orcid.org/0000-0003-4494-0267)
Михаил С. Новиков (ORCID: https://orcid.org/0000-0001-5106-4723)

Institutions

St Petersburg University (RU)

Publication Details

Journal: Organic Letters
Published: 2026-07-26
DOI: https://doi.org/10.1021/acs.orglett.6c02605
Primary Topic: Synthesis and Characterization of Pyrroles
Type: article
Field-Weighted Citation Impact: 0.00

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article

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

Alexander F. Khlebnikov, Pavel O. Kuliaev, Anastasiya V. Agafonova, Ilia A. Smetanin et al.

Jul 26, 2026

Organic Letters

Synthesis and Characterization of Pyrroles

article

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

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

July 26, 2026article en

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.

Organic Letters

St Petersburg University (RU)

Openalex Percentile: Top 16%

Synthesis and Characterization of Pyrroles

DOI Source OpenAlex

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