Rh(II)‐Catalyzed Cascade Cyclization Between Azidobenzoic Acids and Diazopyrazolones for Construction of Spirobenzo[ d ][1,3]oxazin‐4‐ones

Q: What does this research mean for the field?

A Rh(II)-catalyzed cascade cyclization between azidobenzoic acids and diazopyrazolones enables the construction of spirobenzo[d][1,3]oxazin-4-ones in reasonable yields. Novelty: ClaimNovelty.METHODOLOGICAL. Consensus alignment: ConsensusAlignment.NEUTRAL.

Zhi‐Yu Wang; Ya‐Hui Wang; Yu‐Hang Mi; Ya‐Qi Yang; Hong‐Wu Zhao

doi:10.1002/ejoc.70842

September 11, 2026European Journal of Organic Chemistry

Rh(II)‐Catalyzed Cascade Cyclization Between Azidobenzoic Acids and Diazopyrazolones for Construction of Spirobenzo[ d ][1,3]oxazin‐4‐ones

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Key Points

Develop an efficient catalytic cascade cyclization strategy between azidobenzoic acids and diazopyrazolones to construct complex spirobenzo[d][1,3]oxazin-4-one scaffolds.
Conducted reactions using 10 mol% Rh2(OAc)4, 10 mol% Cu(I)OTf, and 20 mol% isoPr-PHOX ligand L13 in 1,2-dichloroethane at 80 °C.
Characterized the resulting molecular architecture using single-crystal X-ray diffraction analysis and chemical inference.
Achieved smooth cascade cyclization yielding spirobenzo[d][1,3]oxazin-4-ones in reasonable chemical yields.
Confirmed the exact three-dimensional structure and connectivity of the spirocyclic product via single-crystal X-ray diffraction analysis.

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Implication

Chemical synthesis study demonstrates catalytic cascade cyclization to construct spirooxazinones, indicating a practical route for complex heterocycle assembly.

Abstract

In the presence of Rh(II) 2 (OAc) 4 (10 mol%), Cu(I)OTf (10 mol%), and iso Pr‐PHOX L13 (20 mol%) in 1,2‐dichloroethane at 80 °C, the cascade cyclization between azidobenzoic acids and diazopyrazolones proceeded readily and furnished spirobenzo[ d ][1,3]oxazin‐4‐ones in reasonable chemical yields. The chemical structure of one compound has been confirmed by X‐ray diffraction analysis, and the others are suggested by inference.

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Wang et al. (2026) studied this question.

synapsesocial.com/papers/6aa7b29f0926e14a848b11a7 https://doi.org/10.1002/ejoc.70842

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Rh(II)‐Catalyzed Cascade Cyclization Between Azidobenzoic Acids and Diazopyrazolones for Construction of Spirobenzo[ d ][1,3]oxazin‐4‐ones

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Rh(II)‐Catalyzed Cascade Cyclization Between Azidobenzoic Acids and Diazopyrazolones for Construction of Spirobenzo[ d ][1,3]oxazin‐4‐ones

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