Nazarov Cyclization of Divinyl and Arylvinyl Epoxides: Application in the Synthesis of Resveratrol‐Based Natural Products

Sudhakar, Gangarajula; Kovela, Satish

doi:10.1002/chem.201500362

Cited by 36 publications

(12 citation statements)

References 66 publications

(30 reference statements)

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“…Therefore, the pentadienyl cation is no longer stabilized by the nitrogen atom. Additionally, steric effect and ring strain of the aziridine, similar to its oxirane variation, 8 would also leverage cyclization.…”

Section: Resultsmentioning

confidence: 99%

“…With our interest in Nazarov cyclization (NC) from alternative pentadienyl precursors, we have recently reported dienylepoxides as a novel Nazarov cyclization precursors from developing efficient method, reacting divinylketone with Darzens reaction conditions and followed by Nazarov cyclization (Figure 1a). 8 We then anticipated that the aza-Darzens reaction of divinyl imines can offer divinylaziridines, subsequent Nazarov cyclization can provide cyclopentadienyl/ indenyl glycines as shown in Figure 1b. Herein, we report the first utilization of dienylaziridines as Nazarov cyclization precusors to give a novel class of indenyl glycines, cyclopentadienyl glycines, including asymmetric version.…”

Section: Introductionmentioning

confidence: 99%

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Nazarov cyclization of dienylaziridines: synthesis of cyclopentadienyl/hydrinedienyl/indenyl glycines

Sudhakar

Reddy

Nanubolu³

2015

Org. Biomol. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Nazarov cyclization of dienylaziridines: synthesis of cyclopentadienyl/hydrinedienyl/indenyl glycines

Sudhakar

Reddy

Nanubolu³

2015

Org. Biomol. Chem.

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“…Sudhakar and Satish reported a new variation of the combination type of Nazarov cyclization: preparation of arylvinylepoxide 32 from divinyl ketone 31 and subsequent Nazarov‐type cyclization, following the ring‐opening reaction of the epoxy ring in the presence of TiCl 4 , to give the cyclopentadiene derivative 33 (Figure ) 14…”

Section: Recent Trends In Nazarov Cyclizationmentioning

confidence: 99%

Recent Progress on Nazarov Cyclizations: The Use of Iron Salts as Catalysts in Ionic Liquid Solvent Systems

Itoh

Nokami

Kawatsura

2016

The Chemical Record

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Nazarov cyclization is an important and versatile method for the synthesis of five-membered carbocycles, and extensive studies have been conducted to optimize the reaction. Among recent studies, several trends are recognized. One is the combination of different reactions with Nazarov cyclization in a one-pot reaction system which enables the preparation of unique cyclization products. The second is the use of a transition-metal catalyst, though Lewis or Brønsted acids have generally been used for the reaction. The third is the realization of the asymmetric Nazarov cyclization. The fourth is the base-catalyzed Nazarov cyclization. Furthermore, several useful protocols for realizing Nazarov cyclization have also been developed. The recent progress on Nazarov cyclizations is summarized in Section 2. Section 3 is our chronicle in this field. We focused on the use of iron as the catalyst in Nazarov cyclizations and ionic liquids as solvents: Nazarov cyclization of thiophene derivatives using FeCl3 as the catalyst was accomplished and we succeeded in demonstrating the first example of an iron-catalyzed asymmetric Nazarov reaction. We next established Nazarov cyclization of pyrrole or indole derivatives using Fe(ClO4 )3 ·Al2 O3 as the catalyst with high trans selectivities in excellent yields. Since the cyclized product was reacted with a vinyl ketone in the presence of the same iron salt, the system allowed realization of the sequential type of Nazarov/Michael reaction of pyrrole derivatives. Furthermore, we demonstrated the recyclable use of the iron catalyst and obtained the desired Nazarov/Michael reaction products in good yields for five repetitions of the reactions without any addition of the catalyst using an ionic liquid, [bmim][NTf2 ], as the solvent. We expect that the iron-catalyzed Nazarov cyclization, in particular, in an ionic liquid solvent might become a useful method to synthesize functional molecules that include cycloalkene moieties.

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“…The formed epoxides [2] , [3] , [4] , [5] , [6] represent an extremely useful intermediate which could be converted to higher value chemical compounds [7] . Moreover, epoxides are present in a large range of natural products [ 8 , 9 ] and biologically active compounds [10] , [11] , [12] , [13] . Epoxides can be accessed in numerous ways, but the most common method consist the epoxidation of olefins using peracids [14] .…”

Section: Introductionmentioning

confidence: 99%

Chemical reactivities and molecular docking studies of parthenolide with the main protease of HEP-G2 and SARS-CoV-2

Aitouna

Belghiti

Eşme

et al. 2021

Journal of Molecular Structure

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We have used bioinformatics to identify drugs for the treatment of COVID-19, using drugs already being tested for the treatment as benchmarks like Remdesivir and Chloroquine. Our findings provide further support for drugs that are already being explored as therapeutic agents for the treatment of COVID-19 and identify promising new targets that merit further investigation. In addition, the epoxidation of Parthenolide 1 using peracids, has been scrutinized within the MEDT at the B3LYP/6-311(d,p) computational level. DFT results showed a high chemoselectivity on the double bond C 3 =C 4 , in full agreement with the experimental outcomes. ELF analysis demonstrated that epoxidation reaction took place through a one-step mechanism, in which the formation of the two new C-O single bonds is somewhat asynchronous.

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Nazarov Cyclization of Divinyl and Arylvinyl Epoxides: Application in the Synthesis of Resveratrol‐Based Natural Products

Cited by 36 publications

References 66 publications

Nazarov cyclization of dienylaziridines: synthesis of cyclopentadienyl/hydrinedienyl/indenyl glycines

Nazarov cyclization of dienylaziridines: synthesis of cyclopentadienyl/hydrinedienyl/indenyl glycines

Recent Progress on Nazarov Cyclizations: The Use of Iron Salts as Catalysts in Ionic Liquid Solvent Systems

Chemical reactivities and molecular docking studies of parthenolide with the main protease of HEP-G2 and SARS-CoV-2

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