Synthesis of novel phosphorus heterocycles: 1,3-dihydro-2,1-benzoxaphosphole 1-oxides

Miles, J. A. L.; Grabiak, Raymond C.; Cummins, Clark H.

doi:10.1021/jo00348a013

Cited by 28 publications

(35 citation statements)

References 2 publications

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“…Similar to the preparation of phosphine oxides, a large number of methods exist for the synthesis of aryl phosphinates and aryl phosphonates . Acyclic dialkyl arylphosphonates II are accessed by the Arbuzov reaction between trialkylphosphites and aryl halides (Scheme , A).…”

Section: Resultsmentioning

confidence: 99%

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

2020

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Phosphine oxides and related phosphorus-containing functional groups such as phosphonates and phosphinates are established structural motifs that are still underrepresented in today’s drug discovery projects, and only few examples can be found among approved drugs. In this account, the physicochemical and in vitro properties of phosphine oxides and related phosphorus-containing functional groups are reported and compared to more commonly used structural motifs in drug discovery. Furthermore, the impact on the physicochemical properties of a real drug scaffold is exemplified by a series of phosphorus-containing analogs of imatinib. We demonstrate that phosphine oxides are highly polar functional groups leading to high solubility and metabolic stability but occasionally at the cost of reduced permeability. We conclude that phosphine oxides and related phosphorus-containing functional groups are valuable polar structural elements and that they deserve to be considered as a routine part of every medicinal chemist’s toolbox.

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Section: Resultsmentioning

confidence: 99%

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

2020

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“…The reactions in the scheme were straightforward except for the coupling reaction between the aryl iodide and dimethyl phenylphosphonite. Nickel chloride was not an effective catalyst, but with palladium acetate or palladium chloride as the catalyst, the reaction proceeded smoothly and provided the desired product in 82% yield . The identity of 9 was established by spectroscopic data and elemental analysis.…”

Section: Resultsmentioning

confidence: 99%

Transition Structure Geometries for Transfers of Neutral and Anionic Nitrogen to Lithiated Carbanions

Beak

Basu

1999

J. Org. Chem.

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The geometries of nucleophilic substitutions at neutral and anionic nitrogen by organolithium species have been investigated. The demonstration of an intramolecular conversion of 9 to 10 provides an endocyclic restriction test which supports a trigonal bipyramidal transition structure for nitrogen transfer. A lack of isotopic scrambling of 12a-18 O during nitrogen transfer is taken to rule out reaction via an oriented ion pair. Attempted endocyclic restriction tests for transfers of formally anionic nitrogen with 32 and 33 were not successful. Reactions of n-butyl, s-butyl and tert-butyllithium reagents with 16, 23, 30, 31, and 36−38 generally afford higher yields with increasing substitution at the carbon of the organolithium reagent and with decreasing substitution adjacent to the nitrogen of the aminating reagent. These results are consistent with trigonal bipyramidal transition states for nucleophilic displacements of oxygen by carbon at neutral and anionic nitrogen.

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“…Ivanov and Ageeva initiated those reactions leading, after rearrangement, according to the authors, to cyclic phosphites. 31 The proposed mechanism was first called into question by Miles et al 32 and was later confirmed by means of NMR analysis by Chasar. 33 The latter author could show that phosphonates were formed when o-hydroxybenzyl phenols reacted with trialkyl phosphites in DMF.…”

Section: Synthesis Of the Phosphonic Acids 7-10mentioning

confidence: 96%

Synthesis of New Benzylic Di-, Tri-, and Tetraphosphonic Acids as Potential Chelating Agents

Aliouane

Hélesbeux

Douadi

et al. 2011

Phosphorus, Sulfur, and Silicon and the Related Elements

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Synthesis of novel phosphorus heterocycles: 1,3-dihydro-2,1-benzoxaphosphole 1-oxides

Cited by 28 publications

References 2 publications

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

Transition Structure Geometries for Transfers of Neutral and Anionic Nitrogen to Lithiated Carbanions

Synthesis of New Benzylic Di-, Tri-, and Tetraphosphonic Acids as Potential Chelating Agents

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