One-pot catalyst-free synthesis of benzopyrroxazine derivatives by a mutually activated sequential annulation process

A one-pot catalyst-free reaction of o -hydroxyaryl azomethine ylides, vinyl pyridines and paraformaldehyde for the synthesis of benzopyrroxazines is reported, which offers a straightforward and atom-economical procedure for the preparation of benzopyrroxazine derivatives in moderate to excellent yie...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-06, Vol.2 (23), p.479-4713
Main Authors: Li, Fu-Qiang, Xie, Pu-Yuan, Chen, Hui-Yu, Bian, Ming, Gao, Yu-Ning, Liu, Zhen-Jiang
Format: Article
Language:English
Subjects:
Catalysts
Chemical reactions
Chemical synthesis
Organic chemistry
Pyridines
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Summary:A one-pot catalyst-free reaction of o -hydroxyaryl azomethine ylides, vinyl pyridines and paraformaldehyde for the synthesis of benzopyrroxazines is reported, which offers a straightforward and atom-economical procedure for the preparation of benzopyrroxazine derivatives in moderate to excellent yields under mild conditions. A self-catalyzed [3 + 2] annulation through a mutual activation method and a sequential non-catalyzed [5 + 1] annulation process contribute to this strategy. The corresponding control experiments have been conducted to reveal the mechanism of this reaction. A one-pot catalyst-free synthetic method of benzopyrroxazine derivatives is reported, which relies on an efficient self-catalyzed [3 + 2] cycloaddition process.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00735e