A Novel Synthesis of New 3-Aryl-7-methylpyrano[4,3-b]pyran-4H,5H-diones Using Hypervalent Iodine(III) Reagents

Prakash, Om; Kumar, Ajay; Sadana, Anil K.; Singh, S. P.

doi:10.1055/s-2005-921751

Cited by 15 publications

(6 citation statements)

References 5 publications

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“…In particular, the key intermediate product 275 in the synthesis of wighteone was prepared by the oxidative rearrangement of 3′-iodotetraalkoxychalcone 274 ,603 and the key step in the synthesis of (±)-indatraline involved the HTIB promoted diastereoselective ring contraction of a 1,2-dihydronaphthalene 276 to construct the indane ring system 277 (Scheme 89). 604 A similar oxidative rearrangement of 3-cinnamoyl-4-hydroxy-6-methyl-2 H -pyran-2-ones with HTIB in dichloromethane followed by cyclization was used by Prakash and co-workers for the direct conversion of o -hydroxychalcones into isoflavone derivatives 605…”

Section: Iodine(iii) Compoundsmentioning

confidence: 99%

Chemistry of Polyvalent Iodine

2008

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Section: Iodine(iii) Compoundsmentioning

confidence: 99%

Chemistry of Polyvalent Iodine

2008

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“…In 2006, Prakash and co‐workers outlined the construction of 3‐aryl‐7‐methylpyrano[4,3‐b]pyran‐4H,5H‐diones 142 (isoflavone analogues of DHA) in good yields (52–59 %) by HTIB mediated 1,2‐aryl shift as well as oxidative cyclization of chalcone analogues of DHA 141 , using dichloromethane as a solvent (Scheme 49). [98] …”

Section: Synthesis Of Heterocyclic Compounds Via Oxidative Cyclizationmentioning

confidence: 99%

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

et al. 2022

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Organo hypervalent iodine reagents are nowadays more attractive and versatile reagents for various chemical transformations in synthetic organic chemistry. These reagents are milder and having similar reactivity compared with toxic heavy metal reagents. Organo hypervalent iodine (λ3) reagents are successfully utilized to prepare synthetically and biologically important heterocycles. Hydroxy(tosyloxy)iodobenzene (HTIB) also acknowledged as Koser's reagent uses as an environmentally sustainable alternative to toxic heavy metals for the numerous and valuable organic transformations. The goal of this review is to highlight the recent advancements of the HTIB especially in the construction of heterocycles with various substitution patterns in a well‐organized form via tosyloxylation of ketones and oxidative cyclization methodology. This review compiles the up‐to‐date synthetic advancements of HTIB in the field of heterocycles.

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“…Different ɑ,β-unsaturated carbonyl compounds of DHAA (chalcones) were prepared by condensation of different aryl aldehyde in methanol in the presence of piperidine. [29][30][31][32] DHAA (1) and its chalcone (2) were reacted separately with ɑ-bromoketones to obtain the desired furo [3,2-c]pyran-4-ones scaffold containing aroyl and styryl moiety.…”

Section: Chemistrymentioning

confidence: 99%

Design and synthesis of highly oxygenated furo[3,2‐c]pyran‐4‐ones and furo[3,2‐c]chromen‐4‐ones scaffold as anticancer and antimicrobial agents

Rani

Kumar

Kamra

et al. 2021

Journal of Heterocyclic Chem

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Synthesis of a number of highly oxygenated furo [3,2-c]pyran/chromen-4-one has been accomplished by one-pot reaction from easily available dehydroacetic acid/3-acetyl-4-hydroxycoumarin or their chalcones and α-bromoketones. All the synthesized molecules were characterized utilizing various spectroscopic techniques and screened for anticancer activity (in vitro) against three colon (HCT-116, SW-620, HT-24), lung (A-549), prostate-(PC-3), breast (MCF-7) cell lines. Compounds 5a, 9d, 9f showed good activity against breast MCF-7 cancer cell line having IC 50 values 6.9, 2.8, 5.3 μM, respectively. Of these compounds, 9d showed better activity against prostate PC-3 cell line with IC 50 value 3.8 μM. The synthesized compounds were also studied for antibacterial activity (in vitro) using different strains of bacteria (Bacillus subtilis and Staphylococcus aureus -Gram-positive and Escherichia coli, Pseudomonas aeruginosa -Gram negative) as well as fungal strains (Aspergillus niger and Candida albicans) using Norfloxacin and Fluconazole as antibacterial and antifungal standard drugs, respectively. The antimicrobial screening study showed that compound 9f exhibited promising activity against S. aureus and B. subtilis, while 5h showed excellent and 5i and 9b showed better activity against E. coli. Compounds 5d and 5e showed promising activity against P. aeruginosa. The compounds 5c-5e displayed excellent activity against C. albicans and A. niger than Fluconazole.

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A Novel Synthesis of New 3-Aryl-7-methylpyrano[4,3-b]pyran-4H,5H-diones Using Hypervalent Iodine(III) Reagents

Abstract: Oxidation of 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones with [hydroxy(tosyloxy)iodo]benzene in CH 2 Cl 2 leads to cyclization, thereby providing a new and convenient route for the synthesis of 3-aryl-7-methylpyrano[4,3-b]pyran-4H,5H-diones.

Cited by 15 publications

References 5 publications

Chemistry of Polyvalent Iodine

Chemistry of Polyvalent Iodine

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

Design and synthesis of highly oxygenated furo[3,2‐c]pyran‐4‐ones and furo[3,2‐c]chromen‐4‐ones scaffold as anticancer and antimicrobial agents

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