Iodine-catalyzed oxidative annulation: facile synthesis of pyrazolooxepinopyrazolones <i>via</i> methyl azaarene sp<sup>3</sup> C–H functionalization

Zhang, Xin‐Ke; Miao, Xiaoyu; Zhou, Yu; Wang, Yumei; Song, Yingchun; Hang, Liu; Xiong, Yi-Lu; Li, Lingyu; Wu, An‐Xin; Zhu, Yan‐Ping

doi:10.1039/d1ob02436a

Cited by 7 publications

(2 citation statements)

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“…Seven membered O-heterocycles 52 were found in nature and show several bioactivities like anticancer, anti-mycobacterial and antifungal activities. Zhang and Zhu et al in 2022 reported a multi-component approach for the synthesis of fused seven-membered oxygen heterocycles; pyrazolooxepinopyrazolones 146 were obtained from the reaction of methyl azaarene 20 and dihydropyrazolones 145 in the iodine–DMSO medium (Scheme 35).…”

Section: Kornblum Oxidationmentioning

confidence: 99%

“…Zhang and Zhu et al in 2022 reported a multi-component approach for the synthesis of fused seven-membered oxygen heterocycles; pyrazolooxepinopyrazolones 146 were obtained from the reaction of methyl azaarene 20 and dihydropyrazolones 145 in the iodine–DMSO medium (Scheme 35). 52 During the optimization study various acid additives such as TfOH, AcOH, HCl, TsOH and TFA were investigated. The best result was obtained in the presence of 2.0 equivalents of TFA.…”

Section: Kornblum Oxidationmentioning

confidence: 99%

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Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

Acharya,

Patra,

Barad

et al. 2024

New J. Chem.

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Section: Kornblum Oxidationmentioning

confidence: 99%

Section: Kornblum Oxidationmentioning

confidence: 99%

Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

Acharya,

Patra,

Barad

et al. 2024

New J. Chem.

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Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds

et al. 2022

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C(sp 3 )À H functionalization is a core part of organic chemistry because of the presence of C(sp 3 )À H bonds in various organic molecules. However, since most C(sp 3 )À H bonds are non-reactive, their functionalization is an uphill task. Standard methods of functionalization employ prefunctionalized reactants, expensive organometallic reagents, strong acids or bases and similar other harsh reaction conditions. These methods eventually affect the reaction and prevent it from yielding optimum results. Transition metalbased catalysts like Pd, Rh and Ru provide a direct functionalization route without unwanted pre-functionalization steps. These catalysts furnish superior results under mild reaction conditions. But, their expense, toxicity and low natural abundance prevent them from achieving ideality. Therefore, 3d transition metal catalysts like Mn, Fe, Co, Ni and Cu catalysts have gained significance as an alternative for conventional transition metal catalysts due to their high natural abundance, low toxicity and affordability. Copperbased catalysts are particularly important owing to the wide range of oxidation states of copper and the facile tunability of their catalytic properties. Hence, an immense amount of research is being conducted on the catalytic activity of copper for C(sp 3 )À H functionalization. This review aims to provide a detailed overview of some recent reports on C(sp 3 )À H functionalization using catalytic systems based on copper.

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Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Reetu,

Kalita,

Dash

et al. 2024

ChemistrySelect

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Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis of the use of iodine and DMSO in various synthetic routes for the preparation of valuable targets are presented. These methods reduce the acceptance on expensive additives and reagents, and offer a more sustainable solution for the synthesis of these important chemical scaffolds.

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Iodine-catalyzed oxidative annulation: facile synthesis of pyrazolooxepinopyrazolones via methyl azaarene sp³ C–H functionalization

Abstract: An iodine-catalytic methyl azaarenes sp3 C-H functionalization has been developed for synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a...

Cited by 7 publications

References 59 publications

Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

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Iodine-catalyzed oxidative annulation: facile synthesis of pyrazolooxepinopyrazolones via methyl azaarene sp3 C–H functionalization

Abstract: An iodine-catalytic methyl azaarenes sp3 C-H functionalization has been developed for synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a...

Cited by 7 publications

References 59 publications

Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation

Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp3)−H Bonds

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

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Product

Resources

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Iodine-catalyzed oxidative annulation: facile synthesis of pyrazolooxepinopyrazolones via methyl azaarene sp³ C–H functionalization

Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds