PhI(OAc)<sub>2</sub>-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

N′-Benzylidene-N-homoallylacetohydrazides were designed and synthesized as novel skeletons for the construction of functionalized tetrahydropyridazines. A series of aryl-and alkylsulfonylated tetrahydropyridazines were obtained in yields of up to 94% employing sulfonyl chlorides as the sulfonyl radical sources under visible-light irradiation. Besides, sulfonylated dihydropyrazoles were also produced from N-allyl-N′-benzylideneacetohydrazides. Mechanistic investigations indicated that both energy transfer and single electron transfer processes were involved in accomplishing the radical 6/5-endo-trig cyclization to the C�N bond.A s a member of nitrogen-containing heterocycles, tetrahydropyridazine represents as a valuable motif in many natural products and pharmacologically active compounds. 1,2a,c The tetrahydropyridazine-containing structures play diverse pharmacological roles in a large number of biologically active molecules that function as nonsteroidal progesterone receptors, influenza neuraminidase inhibitors, cardiotonic agents, etc. (Figure 1). 2 Besides, the tetrahydropyridazines can also be Letter pubs.acs.org/OrgLett

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Advances in the synthesis of functionalized tetrahydropyridazines from hydrazones

Yu,

Pan

2024

Org. Biomol. Chem.

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PhI(OAc)₂-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

Abstract: A metal-free protocol for the direct construction of C(sp2)–N and C–O bonds via a PhI(OAc)2-mediated dehydrogenative aminoacyloxylation of β,γ-unsaturated hydrazones with Togni reagent II is reported.

Cited by 4 publications

References 39 publications

Organoiodine-mediated dehydrogenative N–N coupling of aryl alkoxycarbamates

Organoiodine-mediated dehydrogenative N–N coupling of aryl alkoxycarbamates

Photocatalytic Carbosulfonylation/Cyclization of N-Homoallyl and N-Allyl Aldehyde Hydrazones toward Sulfonylated Tetrahydropyridazines and Dihydropyrazoles

Advances in the synthesis of functionalized tetrahydropyridazines from hydrazones

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PhI(OAc)2-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

Abstract: A metal-free protocol for the direct construction of C(sp2)–N and C–O bonds via a PhI(OAc)2-mediated dehydrogenative aminoacyloxylation of β,γ-unsaturated hydrazones with Togni reagent II is reported.

Cited by 4 publications

References 39 publications

Organoiodine-mediated dehydrogenative N–N coupling of aryl alkoxycarbamates

Organoiodine-mediated dehydrogenative N–N coupling of aryl alkoxycarbamates

Photocatalytic Carbosulfonylation/Cyclization of N-Homoallyl and N-Allyl Aldehyde Hydrazones toward Sulfonylated Tetrahydropyridazines and Dihydropyrazoles

Advances in the synthesis of functionalized tetrahydropyridazines from hydrazones

Contact Info

Product

Resources

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PhI(OAc)₂-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor