2,4,6-Tris(4-iodophenoxy)-1,3,5-triazine as a new recyclable “iodoarene” for in situ generation of hypervalent iodine(III) reagent for α-tosyloxylation of enolizable ketones

Thorat, Prerana B.; Bhong, Bhagyashree Y.; Shelke, Amol V.; Karade, Nandkishor N.

doi:10.1016/j.tetlet.2014.04.052

Cited by 11 publications

(3 citation statements)

References 43 publications

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“…Karade and co‐workers [39] reported a strategy for the synthesis of 2,4,6‐tris(4‐iodophenoxy)‐1,3,5‐triazine as shown in Scheme 16. Different reaction parameters were studied and final products were obtained using 2,4,6‐trichloro‐1,3,5‐triazine 48 with a mixture of 4‐iodophenol 49 in a molar ratio of 1 : 3 using potassium hydroxide as alkali and acetone as the reaction medium at ambient temperature.…”

Section: Miscellaneous Strategiesmentioning

confidence: 99%

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Rathod,

Pawar,

Puri

et al. 2024

ChemistrySelect

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Nitrogen‐bearing heterocycles are ubiquitous in landscapes and have a great impact on living nature. Structural motifs are present in diverse natural products like vitamins, antibiotics, and alkaloids, as well as pharmaceuticals. The 1,3,5‐Triazines are the primitive class of heterocyclic motifs and are used in various synthetic and medicinal applications. This review covers an exhaustive exploration of literature reports and describes various synthetic strategies and pharmacological activities of 1,3,5‐triazine moiety. Synthetic strategies include multicomponent reaction, metal catalyst reaction, microwave‐assisted strategy, etc. to construct 1,3,5‐triazine moiety. Pharmacological activities include anticancer, antimalarial, antibacterial, antifungal, antiviral, anti‐tubercular, anti‐leishmanial, anti‐inflammatory, histamine antagonist, serotonin antagonist, etc. For anticancer activity, 1,3,5‐triazine moiety‐containing compounds were tested on different cell lines, and inhibitory activity was also mentioned. The involvement of this scaffold in the treatment of various diseases and disorders makes this scaffold important from a research perspective. Therefore, there is a need to present the combined data of research and reviews to the researchers to develop new molecules. For that reason, the review included information from articles published from 1978 onwards.

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Section: Miscellaneous Strategiesmentioning

confidence: 99%

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Rathod,

Pawar,

Puri

et al. 2024

ChemistrySelect

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“…Tosyloxylation of ketones in 63-84% yield can be performed using 2,4,6-tris[(4-iodo)phenoxy]-1,3,5-triazine (127) as the catalyst. 73 In 2015, Kita and co-workers achieved the cross-coupling of pyrroles 128 and azoles 129 to afford coupling product 130 in 52-78% yield using 1,3,5,7-tetrakis [4-(diacetoxyiodo)phenyl]adamantane (80) in combination with bromotrimethylsilane at 70 °C (Scheme 21). 74 In 2018, Kita et al reported the cross-coupling reaction of pyrroles 131 with the electron-rich arene 132 using adamantane-core-based reagent 80 in hexafluoroisopropanol (HFIP) at room temperature (Scheme 22).…”

Section: Review Synthesismentioning

confidence: 99%

“…72 α-Tosyloxylation of ketones in 63–84% yield can be performed using 2,4,6-tris[(4-iodo)phenoxy]-1,3,5-triazine ( 127 ) as the catalyst. 73…”

Section: Non-polymeric Recyclable Hypervalent Iodine Reagentsmentioning

confidence: 99%

Recyclable Hypervalent Iodine Reagents in Modern Organic Synthesis

et al. 2022

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Hypervalent iodine (HVI) reagents have gained much attention as versatile oxidants because of their low toxicity, mild reactivity, easy handling, and availability. Despite their unique reactivity and other advantageous properties, stoichiometric HVI reagents are associated with the disadvantage of generating non-recyclable iodoarenes as waste/co-products. To overcome these drawbacks, the syntheses and utilization of various recyclable hypervalent iodine reagents have been established in recent years. This review summarizes the development of various recyclable non-polymeric, polymer-supported, ionic-liquid-supported, and metal–organic framework (MOF)-hybridized HVI reagents.1 Introduction2 Polymer-Supported Hypervalent Iodine Reagents2.1 Polymer-Supported Hypervalent Iodine(III) Reagents2.2 Polymer-Supported Hypervalent Iodine(V) Reagents3 Non-Polymeric Recyclable Hypervalent Iodine Reagents3.1 Non-Polymeric Recyclable Hypervalent Iodine(III) Reagents3.2 Recyclable Non-Polymeric Hypervalent Iodine(V) Reagents3.3 Fluorous Hypervalent Iodine Reagents4 Ionic-Liquid/Ion-Supported Hypervalent Iodine Reagents5 Metal–Organic Framework (MOF)-Hybridized Hypervalent Iodine Reagents6 Conclusion

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Recyclable Magnetic Nanoparticle‐Supported Iodoarene Catalysts for Oxidation of 4‐Alkoxyphenols to Quinones

et al. 2016

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Iodoarene catalysts immobilizedo nm agnetite (Fe 3 O 4 )w ered eveloped. The reactivity of catalysts 4a and 4b were similart ot hat of 4-iodophenoxyacetic acid (3) for the oxidation of 4-alkoxyphenols in the presence of Oxone as ac o-oxidant to give the corresponding p-quinones in high yields. In addition, 4b was readily recovered by the use of an external magneta nd was recycled up to eight times.T his is the first example of am agnetic, nanoparticle-supported iodoarene catalyst.

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2,4,6-Tris(4-iodophenoxy)-1,3,5-triazine as a new recyclable “iodoarene” for in situ generation of hypervalent iodine(III) reagent for α-tosyloxylation of enolizable ketones

Cited by 11 publications

References 43 publications

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Recyclable Hypervalent Iodine Reagents in Modern Organic Synthesis

Recyclable Magnetic Nanoparticle‐Supported Iodoarene Catalysts for Oxidation of 4‐Alkoxyphenols to Quinones

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