ChemInform Abstract: SYNTH. VON TRIS‐(N,N‐DIMETHYL‐2‐CARBAMOYLAETHYL)‐PHOSPHINOXID

Daigle, Donald J.; Vigo, Tyrone L.; Chance, Leon H.

doi:10.1002/chin.197314381

Cited by 3 publications

(4 citation statements)

References 1 publication

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“…Elemental analyses were performed in-house using a LECO CHNS-932 microanalyser. The phosphanes PTA [59] and [pymePTA]Br [46] (4) and gold derivatives [AuCl(tht)], [60] [Au(SCN)(tht)] [61] and [Au(C 6 F 5 )(tht)] [60] were synthesized as described elsewhere. All chemicals were reagent-grade and used as received from commercial suppliers.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Gold(I) Derivatives Bearing Alkylated 1,3,5‐Triaza‐7‐phosphaadamantane as Selective Anticancer Metallodrugs

et al. 2016

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The alkylation of one of the nitrogen atoms of the molecule 1,3,5,triaza‐7‐phosphaadamantane (PTA) with para‐substituted benzylic units and the l‐phenylalanine methyl ester moiety are reported. The crystalline structures of the two alkylated PTA species [PTA‐CH2‐p‐COOH‐C6H4]Br (1a) and [PTA‐CH2‐p‐CH2COOH‐C6H4]Br (2) reveal the presence of interactions between the bromide anion and the OH group of the acid moiety. Bis‐phosphane derivatives were prepared by the alkylation of two PTA molecules with a dibromide salt to afford more water‐soluble species. The corresponding mono‐ and dinuclear chloro‐, thiocyanato‐ and pentafluorophenyl gold(I) derivatives are described. Most of the new complexes have been tested as anticancer agents, exhibiting higher cytotoxicity than cisplatin against human colon cancer cell lines. Some of them display low cytotoxicity towards differentiated cells (non‐carcinogenic), as determined from viability studies, thereby demonstrating a significant specificity in this type of cancer.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Gold(I) Derivatives Bearing Alkylated 1,3,5‐Triaza‐7‐phosphaadamantane as Selective Anticancer Metallodrugs

et al. 2016

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“…PTA was prepared from tetrahydroxymethylphosphonium sulfate according to a previously reported procedure. [7] Nuclear magnetic resonances ( 1 H, 13 C, and 31 P) were recorded on a Bruker 300 MHz NMR spectrometer using TMS as internal standard ( 1 H, 13 C) and 85% phosphoric acid as external standard ( 31 P), unless otherwise mentioned. Elemental analyses were performed on a Yanaco CHN Corder MT-3 automatic analyzer.…”

Section: Methodsmentioning

confidence: 99%

“…[6] It can be easily prepared in high yield from a commercially available material, tetrahydroxymethylphosphonium chloride or sulfate. [7] After its discovery, related research activity had been quiet until recently when it attracted renewed interest due to its properties of water solubility and strong coordinating ability with a wide range of transition metals. [8] In most of the recent reports, PTA has been used as a unique watersoluble phosphine ligand.…”

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confidence: 99%

The First Air‐Stable and Efficient Nucleophilic Trialkylphosphine Organocatalyst for the Baylis–Hillman Reaction

Tang

Chen

et al. 2006

Adv Synth Catal

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1,3,5,-Triaza-7-phosphaadamantane (PTA) is first reported to be a convenient and efficient nucleophilic trialkylphosphine organocatalyst for the Baylis-Hillman reaction. Thus, under the mediation of 15 -20 mol % of PTA and practical conditions, both aromatic and aliphatic aldehydes react with the activated alkenes like acrylates and methyl vinyl ketone to afford the corresponding adducts in fair to excellent yields.

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“…PTA was prepared from tetrahydroxymethylphosphonium sulfate according to a previous procedure. [29] Other phosphorus catalysts were prepared as reported in the literature. 4-Substituted 2,3-butadienoates [30] and N-tosyl-and N-thiophosphinoylimines [31] were also prepared as described in the literature.…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

1,3,5‐Triaza‐7‐phosphaadamantane (PTA): A Practical and Versatile Nucleophilic Phosphine Organocatalyst

Tang

Zhang

et al. 2007

Adv Synth Catal

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In this paper, the air-stable and readily available 1,3,5-triaza-7-phosphaadmantane (PTA) is reported as a practical and versatile nucleophilic phosphine organocatalyst. Under the mediation of 15-30 mol % of PTA, various electrophiles like aldehydes and imines readily undergo the MoritaBaylis-Hillman reactions with a variety of activated olefins, giving the corresponding adducts in high yields. In the phosphine-catalyzed [3 + 2] cycloaddition reaction of 4-substituted 2,3-butadienoates with N-tosylimines, PTA is also proven to be a comparable catalyst as tributylphosphine (PBu 3 ). By systematic comparison with other structurally similar N,P catalysts, it is concluded that the superiority of PTA in the above nucleophilic catalysis is attributable to its comparable nucleophilicity with that of trialkylphosphines. The feasibility to use PTA as an alternative catalyst in place of the air-sensitive trialkylphosphines is also discussed.

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ChemInform Abstract: SYNTH. VON TRIS‐(N,N‐DIMETHYL‐2‐CARBAMOYLAETHYL)‐PHOSPHINOXID

Cited by 3 publications

References 1 publication

Synthesis of Gold(I) Derivatives Bearing Alkylated 1,3,5‐Triaza‐7‐phosphaadamantane as Selective Anticancer Metallodrugs

Synthesis of Gold(I) Derivatives Bearing Alkylated 1,3,5‐Triaza‐7‐phosphaadamantane as Selective Anticancer Metallodrugs

The First Air‐Stable and Efficient Nucleophilic Trialkylphosphine Organocatalyst for the Baylis–Hillman Reaction

1,3,5‐Triaza‐7‐phosphaadamantane (PTA): A Practical and Versatile Nucleophilic Phosphine Organocatalyst

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