Modular Assembly of 2-Aminoaniline Derivatives by Merging Hydroxylamine-Passerini and Hetero-Cope Rearrangement

Yu, Ning; Lv, Jing-Fang; He, Shi-Mei; He, Kui-Cheng; Zheng, Wei-Hao; Zhou, Yu-Qiang; Jiang, Kun; Pan, Xi-Chun; Wei, Ye

doi:10.1021/acs.orglett.3c04270

Org. Lett.

2024

DOI: 10.1021/acs.orglett.3c04270

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Modular Assembly of 2-Aminoaniline Derivatives by Merging Hydroxylamine-Passerini and Hetero-Cope Rearrangement

Ning Yu,

Jing-Fang Lv,

Shi-Mei He

et al.

Abstract: A metal-free three-component protocol that combines a hydroxylamine-Passerini reaction and hetero-Cope rearrangement was realized, which enables the modular assembly of a wide range of structurally new and interesting 2-aminoanilines bearing an α-hydroxyamide substructure.

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Metal-Free Synthesis of Benzisoxazolones Utilizing ortho-Ester and ortho-Cyano-Functionalized Diaryliodonium Salts with Protected Hydroxylamines

Elboray,

Bae,

Kikushima

et al. 2024

J. Org. Chem.

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Herein, we report the development of metal-free one/two-pot procedures for the synthesis of benzo[c]isoxazol-3(1H)-one (benzisoxazolone) heterocycles by designing diaryliodonium salts featuring ortho-ester or nitrile functional groups. These react smoothly with protected hydroxylamines under mild conditions to produce N-arylhydroxylamine intermediates, which readily cyclize to give benzisoxazolone derivatives under acidic conditions. This metal-free process maintains the weak N−O bond, tolerates a wide range of diaryliodonium salts and protected hydroxylamines with diverse functional/ protecting groups, thereby overcoming the challenges associated with previous transformations. The protocol expands the reaction scope and broadens the chemical space of the fused isoxazolone backbones to include unprecedented five-membered heteroaryl-fused isoxazolones in high yields. This method is also applicable to gram-scale synthesis, and the resulting benzisoxazolones can be effectively derivatized at the N-position to afford valuable compounds.

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Metal-Free Synthesis of Benzisoxazolones Utilizing ortho-Ester and ortho-Cyano-Functionalized Diaryliodonium Salts with Protected Hydroxylamines

Elboray,

Bae,

Kikushima

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

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Modular Assembly of 2-Aminoaniline Derivatives by Merging Hydroxylamine-Passerini and Hetero-Cope Rearrangement

Abstract: A metal-free three-component protocol that combines a hydroxylamine-Passerini reaction and hetero-Cope rearrangement was realized, which enables the modular assembly of a wide range of structurally new and interesting 2-aminoanilines bearing an α-hydroxyamide substructure.

Cited by 1 publication

References 49 publications

Metal-Free Synthesis of Benzisoxazolones Utilizing ortho-Ester and ortho-Cyano-Functionalized Diaryliodonium Salts with Protected Hydroxylamines

Metal-Free Synthesis of Benzisoxazolones Utilizing ortho-Ester and ortho-Cyano-Functionalized Diaryliodonium Salts with Protected Hydroxylamines

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