Correction to Copper-Promoted 6-<i>endo-trig</i> Cyclization of β,γ-Unsaturated Hydrazones for the Synthesis of 1,6-Dihydropyridazines

Guo, Yating; Zhao, Mi‐Na; Z, Ren; Zhang, Guan

doi:10.1021/acs.orglett.8b01916

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“…In this context, hydrazones represent an appealing alternative, [21][22][23][24] being easy to prepare and displaying a very peculiar reactivity. [25][26][27][28][29][30] Many synthetic approaches exploiting them have been reported, like Palladium 31,32 and Copper mediated cyclizations, 33,34 but especially, visible light-mediated processes. Photocatalytic transformations have, indeed, attracted huge interest in the last years, disclosing alternative routes to functionalized molecules under mild reaction conditions and with high functional group tolerance.…”

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confidence: 99%

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

et al. 2021

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Tetrahydropyridazines are of particular interest for their versatility as intermediates in organic synthesis and display pharmacological activity in several domains. Here, we describe the photocatalytic synthesis of different tetrahydropyridazines starting from γ,δ-unsaturated Narylsulfonylhydrazones. Simple structural changes of substrates result into three different pathways beginning from a common N-hydrazonyl radical which evolvesthrough a dominocarboamination/dearomatization, a HAT process, or a photoinduced radical Smiles rearrangementto afford diverse tetrahydropyridazines. All reactions are carried out in very mild conditions and quite inexpensive [Ru(bpy)3]Cl2is used as the catalyst. Preliminary mechanism studies are presented, among them luminescence and electrochemical characterization of the involved species. Computational studies allow to rationalize the mechanism in accord with the experimental findings.

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