Synthesis of phosphorus containing medium ring heterocycles by sequential Claisen rearrangement and ring closing metathesis

Majumdar, K. C.; Nandi, Raj Kumar; Ganai, Sintu

doi:10.1016/j.tetlet.2014.01.008

Cited by 15 publications

(7 citation statements)

References 40 publications

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“…Several catalysts have been reported to be tolerant to the presence of heteroatoms and complex or bulky functional groups, and as a result a range of examples of macrocyclic ED‐ROMP precursors are emerging in the literature. Initially, RCM reactions were most commonly employed for the synthesis of complex five‐ to eight‐membered lactams, carbocyclic and heterocyclic vinyl chlorides, alkenylboronates, a variety of phosphorous, sulfur and fluorine containing rings, cyclic di‐ and tri‐nucleotides, and more . Following from these precedents, macrocycle synthesis evolved from simple unsaturated macrolactones and macrolactams, to an even larger range of functional macrocycles such as fluorinated amino and azamacrolactones .…”

Section: Macrocycle Synthesismentioning

confidence: 99%

Recent developments in entropy‐driven ring‐opening metathesis polymerization: Mechanistic considerations, unique functionality, and sequence control

Pearce

Foster

O’Reilly

2019

J. Polym. Sci. Part A: Polym. Chem.

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Entropy‐driven ROMP (ED‐ROMP) involves polymerization of olefin‐containing macrocyclic monomers under entropically favorable conditions. Macrocycles can be prepared from a variety of interesting molecules which, when polymerized, impart unique functionality to the resulting polymer backbone such as degradable linkages, biological moieties, crystallizable groups, or supramolecular hosts. In addition, the sequence of atoms in the cyclic monomer is preserved within the polymer repeating units, allowing for facile preparation of sequence‐defined polymers. In this review article, we consider how the mechanism of ROMP applies to ED polymerizations, how olefinic macrocycles are synthesized, and how polymerization conditions can be tuned to maximize conversion. Recent works in the past 10 years are highlighted, with emphasis on methods which can be employed to achieve fast polymerization kinetics and/or selective head‐to‐tail regiochemistry, thus improving polymerization control. ED‐ROMP, with its unique capability to produce polymers with well‐defined polymer backbone microstructure, represents an essential complement to other, well‐established, metathesis methodologies such as ROMP. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1621–1634

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Section: Macrocycle Synthesismentioning

confidence: 99%

Recent developments in entropy‐driven ring‐opening metathesis polymerization: Mechanistic considerations, unique functionality, and sequence control

Pearce

Foster

O’Reilly

2019

J. Polym. Sci. Part A: Polym. Chem.

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“…The phosphorous heterocycles (PHs) required for our study were prepared according to published procedure using ring closing metathesis reaction [23] . Here, PH-1 is a uracil annulated oxophosphocine derivative whereas PH-2 and PH-3 are differently substituted benzo-oxophosphocine derivatives.…”

Section: Methodsmentioning

confidence: 99%

Binding interaction of phosphorus heterocycles with bovine serum albumin: A biochemical study

Roy

Nandi

Ganai

et al. 2017

Journal of Pharmaceutical Analysis

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Interaction between bovine serum albumin (BSA) and phosphorus heterocycles (PHs) was studied using multi-spectroscopic techniques. The results indicated the high binding affinity of PHs to BSA as it quenches the intrinsic fluorescence of BSA. The experimental data suggested the fluorescence quenching mechanism between PHs and BSA as a dynamic quenching. From the UV–vis studies, the apparent association constant (Kapp) was found to be 9.25×102, 1.27×104 and 9.01×102 L/mol for the interaction of BSA with PH-1, PH-2 and PH-3 respectively. According to the Förster's non-radiation energy transfer (FRET) theory, the binding distances between BSA and PHs were calculated. The binding distances (r) of PH-1, PH-2 and PH-3 were found to be 2.86, 3.03, and 5.12 nm, respectively, indicating energy transfer occurs between BSA and PHs. The binding constants of the PHs obtained from the fluorescence quenching data were found to be decreased with increase of temperature. The negative values of the thermodynamic parameters ΔH, ΔS and ΔG at different temperatures revealed that the binding process is spontaneous; hydrogen bonds and van der Waals interaction were the main force to stabilize the complex. The microenvironment of the protein-binding site was studied by synchronous fluorescence and circular dichroism (CD) techniques and data indicated that the conformation of BSA changed in the presence of PHs. Finally, we studied the BSA-PHs docking using Autodock and results suggest that PHs is located in the cleft between the domains of BSA.

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“…Examples include: (1) formation of an azaborine ring system (e.g. 281) [726]; (2) cyclic phosphonates fused to benzene or heteroaromatic rings [727]; (4) dihydrothiophenes (e.g. 282) [728]; (5) alkenylsultones (e.g.…”

Section: )mentioning

confidence: 99%

“…A more stable osmabenzene was formed by replacing the chloride ligands with thiocyanate ligands. Key events in this transformation involve hydroxide elimination to form the cyclic carbene complex(727), which undergoes ring opening to afford the allenylphosphonium salt(728). Addition of chloride to the vinylphosphonium salt group followed by elimination of triphenylphosphine affords the osmabenzene.…”

mentioning

confidence: 99%

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Herndon

2016

Coordination Chemistry Reviews

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Synthesis of phosphorus containing medium ring heterocycles by sequential Claisen rearrangement and ring closing metathesis

Cited by 15 publications

References 40 publications

Recent developments in entropy‐driven ring‐opening metathesis polymerization: Mechanistic considerations, unique functionality, and sequence control

Recent developments in entropy‐driven ring‐opening metathesis polymerization: Mechanistic considerations, unique functionality, and sequence control

Binding interaction of phosphorus heterocycles with bovine serum albumin: A biochemical study

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

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