Visible Light Mediated Photocatalytic <i>N</i>-Radical Cascade Reactivity of γ,δ-Unsaturated <i>N</i>-Arylsulfonylhydrazones: A General Approach to Structurally Diverse Tetrahydropyridazines

Azzi, Emanuele; Ghigo, Giovanni; Parisotto, Stefano; Pellegrino, Francesco; Priola, Emanuele; Renzi, Polyssena; Deagostino, Annamaria

doi:10.1021/acs.joc.0c02605

Cited by 20 publications

(13 citation statements)

References 94 publications

(154 reference statements)

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“…Employing the similar strategy, Deagostino and co-workers reported an intramolecular dearomatization reaction of arenes with the g,d-unsaturated N-arylsulfonylhydrazones (Scheme 33). 70 Nitrogen-containing aromatic compounds, pyridine, quinoline and isoquinoline for instance, can serve as versatile building blocks in organic synthesis and prominent structural units in many medicinal and synthetically important compounds. One of the well-known radical transformations based on these heteroarenes is the Minisci reaction, which introduces a variety of functional groups onto the aromatic rings with retaining their aromaticity.…”

Section: Shu-li Youmentioning

confidence: 99%

Visible-light induced dearomatization reactions

et al. 2022

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Section: Shu-li Youmentioning

confidence: 99%

Visible-light induced dearomatization reactions

et al. 2022

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“…Deagostino and co-workers 44 described, in 2021, the diastereoselectively preparation of tetrahydropyridazines 15 from ,-unsaturated N-arylsulfonylhydrazones 14 under photocatalytic conditions (Scheme 5). The reaction was successful with both aryl-and alkyl-substituted N-tosyland N-phenylsulfonylhydrazones.…”

Section: Scheme 3 Regioselective N-functionalization Of Pyridinesmentioning

confidence: 99%

Recent Advances in Transition-Metal-Catalyzed Reactions of N-Tosylhydrazones

Pilania¹,

Vaishya²,

Singhal³

et al. 2022

Synthesis

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N-Tosylhydrazones are highly versatile precursors for in situ carbene formation and are frequently used in metal-catalyzed cross-coupling reactions. Due to their many applications in organic synthesis, including C–C, C–O, C–N, and C–S bond formation, N-tosylhydrazones have recently received much interest. They can be simply synthesized by reacting an aldehyde or ketone with N-tosylhydrazine to produce a solid N-tosylhydrazone, which is a ‘green’ precursor of diazo compounds. Using a suitable metal catalyst, N-tosylhydrazones show versatile substrate scope for the synthesis of substituted diaminopyrroles, chromenopyrazoles, alkenylpyrazoles, benzofuran thioethers, tetrahydropyridazines, sulfur-containing heterocycles, and benzofurans with potent biological activities and even regioselective N-functionalization reactions. Metal-catalyzed reactions of N-tosylhydrazones for the construction of bioactive heterocycles are still highly in demand. Hence, this review focuses on the recent synthetic application of N-tosylhydrazones influenced by different transition metals with notable features like simple workup procedures, gram-scale synthesis, broad substrate scope, multicomponent processes, cyclization, and carbon–heteroatom bond formation.1 Introduction2 Applications of N-Tosylhydrazones3 Conclusion

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“…In 2021, Deagostino presented mild photocatalysis of γ,δ-unsaturated hydrazones via domino carboamination/dearomatization, in which a hydrogen atom transter process or light-induced radical Smiles rearrangement is used to produce various tetrahydropyridazines (Scheme 26). [49] Remarkably, under photocatalysis, both electron-rich and electron-deficient aromatic rings can perform the reaction smoothly. Using 2,2-dimethylbut-3-enylphenylmesitylhydrazone 149 a as the substrate, the total yield is 95% and the ratio of 151 a/ 152 a is 53:47.…”

Section: Visible Light-enabled Cyclization Of Hydrazones With Adjacent Unsaturated Bondsmentioning

confidence: 99%

Update on the Synthesis of N‐Heterocycles via Cyclization of Hydrazones (2017–2021)

Meng

et al. 2021

Adv Synth Catal

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Hydrazones, as universal structural units, are useful synthons for the formation of carbonnitrogen and nitrogenÀ heteroatom bonds. Thus, they provide new methods of constructing nitrogen-containing heterocycles. In recent years, especially between 2017 and 2021, many efforts have been made to exploit hydrazone-based reactions in efforts to develop more powerful and effective pathways towards the synthesis of various multifunctional heterocyclic compounds. However, despite the tremendous amount of work that has been published over the past five years, no review has been published that summarizes the significant progress in the preparation of nitrogen heterocycles via intramolecular cyclization of hydrazones with adjacent unsaturated bonds or intermolecular cyclization of hydrazones with unsaturated systems. Therefore, this review summarizes the hydrazone-based cyclization strategies used to synthesize nitrogen-containing heterocycles over the past five years. It discusses the corresponding reaction scopes, limitations, mechanisms, and problems. Cyclization of Hydrazones with Unsaturated Systems 3.3. Cyclization of Hydrazones with Unsaturated Systems Under Metal-Free Conditions 4. Conclusion

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Visible Light Mediated Photocatalytic N-Radical Cascade Reactivity of γ,δ-Unsaturated N-Arylsulfonylhydrazones: A General Approach to Structurally Diverse Tetrahydropyridazines

Cited by 20 publications

References 94 publications

Visible-light induced dearomatization reactions

Visible-light induced dearomatization reactions

Recent Advances in Transition-Metal-Catalyzed Reactions of N-Tosylhydrazones

Update on the Synthesis of N‐Heterocycles via Cyclization of Hydrazones (2017–2021)

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