CCCLXXVII.—The condensation of aromatic amino-sulphonic acids with isocyanic acid, phenylcarbimide, and cyanamide

Scott, John Richard; Cohen, Julius Berend

doi:10.1039/ct9232303177

Cited by 4 publications

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“…Along the same line, reaction of 3-aminobenzoic acid with potassium-cyanate produced 2a . Ligand 2b [3-(3-phenylureido)benzoic acid] was prepared by treating 3-aminobenzoic acid with phenylisocyanate in THF. , Thus, the four ligands with an appended supramolecular motif were prepared in a single step in good to excellent yields.…”

Section: Resultsmentioning

confidence: 99%

“…Ltd. Ligands 1a and 1b were synthesized by modifying a literature procedure . Ligands 2a and 2b were synthesized by improved literature protocols. , Other chemicals, such as [Pd(COD)MeCl] and [Pd(TMEDA)Me 2 ], were synthesized by following known procedures. Ethylene polymerization was carried out in a 250 mL stainless steel high pressure Buchi (glasuster cyclone 075) reactor equipped with a mechanical stirrer and a heating/cooling jacket.…”

Section: Methodsmentioning

confidence: 99%

“…The supramolecular phosphines 1a and 1b were prepared by treating iodourea with diphenylphosphine in almost quantitative yields (90%). 52 The appearance of a 31 P NMR resonance at −6.05 and −5.96 ppm and disappearance of diphenylphosphine resonance clearly indicated formation of 1a and 1b. Along the same line, reaction of 3-aminobenzoic acid with potassiumcyanate produced 2a.…”

Section: ■ Introductionmentioning

confidence: 93%

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H-Bonding Assisted Self-Assembly of Anionic and Neutral Ligand on Metal: A Comprehensive Strategy To Mimic Ditopic Ligands in Olefin Polymerization

et al. 2017

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Self-assembly of two neutral ligands on a metal to mimic bidentate ligand coordination has been frequently encountered in the recent past, but self-assembly of an anionic ligand on a metal template alongside a neutral ligand remains an elusive target. Such a self-assembly is hampered by additional complexity, wherein a highly negatively charged anion can form intermolecular hydrogen bonding with the supramolecular motif, leaving no scope for self-assembly with neutral ligand. Presented here is the self-association of anionic ligand 3-ureidobenzoic acid (2a) and neutral ligand 1-(3-(diphenylphosphanyl)phenyl)urea (1a) on a metal template to yield metal complex [{COOCHNH(CO)NH}{PhPCHNH(CO)NH}PdMeDMSO] (4a). The identity of 4a was established by NMR and mass spectroscopy. Along the same lines, 3-(3-phenylureido)benzoic acid (2b) and 1-(3-(diphenylphosphanyl)phenyl)-3-phenylurea (1b) self-assemble on a metal template to produce palladium complex [{COOCHNH(CO)NHPh}{PhPCHNH(CO)NHPh}PdMePy] (5c). The existence of 5c was confirmed by Job plot, 1-2D NMR spectroscopy, deuterium labeling, IR spectroscopy, UV-vis spectroscopy, model complex synthesis, and DFT calculations. These solution and gas phase investigations authenticated the presence of intramolecular hydrogen bonding between hydrogen's of 1b and carbonyl oxygen of 2b. The generality of the supramolecular approach has been validated by preparing six complexes from four monodentate ligands, and their synthetic utility was demonstrated in ethylene polymerization. Complex 4a was found to be the most active, leading to the production of highly branched polyethylene with a molecular weight of 55700 g/mol and melting temperature of 112 °C.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 93%

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H-Bonding Assisted Self-Assembly of Anionic and Neutral Ligand on Metal: A Comprehensive Strategy To Mimic Ditopic Ligands in Olefin Polymerization

et al. 2017

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“…[16] Thus, treatment of sulfonic acid 5 [17] with acetic anhydride in the presence of pyridine delivered the sulfonate salt 6, as shown in Scheme 2. The subsequent reaction with phosphorus pentachloride followed by treatment of the resultant sulfonyl chloride with aqueous ammonia led to the formation of 7-bromo-benzothiadiazine-S,S-dioxide 7 [18] in 45 % overall yield.…”

Section: Synthesismentioning

confidence: 97%

Synthesis of Modified 4H‐1,2,4‐Benzothiadiazine‐1,1‐dioxides and Determination of their Affinity and Selectivity for Different Types of K_ATP Channels

et al. 2009

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4H-1,2,4-Benzothiadiazine-1,1-dioxides with various substituents in positions 3, 5, and 7 were synthesized and tested as K(ATP) channel agonists in artificial cell systems (CHO cells transfected with SUR1/Kir6.2, and HEK 293 transfected with SUR2B/Kir6.1) as model systems for insulin-secreting pancreatic beta-cells and for smooth muscle cells, respectively. The effects of agonists were tested in intact cells using DiBAC4(3) [bis-(1,3-dibarbituric acid)trimethine oxanol] as a membrane potential dye, and the results compared with their binding affinity for the SUR2B-type K(ATP) channels using the radioligand [(3)H]P1075. Compounds with cycloalkyl and (cycloalkyl)methyl side chains in position 3 had higher affinities towards the SUR2B/Kir6.1 receptor compared with the parent compound diazoxide (1 a). Compounds with bulky, nonpolar residues in position 3 exhibited remarkable selectivity for SUR2B-type K(ATP) channels. The compound substituted with a bulky (1-adamantyl)methyl residue exhibited micromolar affinity and activity on SUR2B-type K(ATP) channels without being able to activate the SUR1-type K(ATP) channels.

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Guanidin, Kreatin, Kreatinin

Sickel¹

1930

Biochemisches Handlexikon

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CCCLXXVII.—The condensation of aromatic amino-sulphonic acids with isocyanic acid, phenylcarbimide, and cyanamide

Cited by 4 publications

References 0 publications

H-Bonding Assisted Self-Assembly of Anionic and Neutral Ligand on Metal: A Comprehensive Strategy To Mimic Ditopic Ligands in Olefin Polymerization

H-Bonding Assisted Self-Assembly of Anionic and Neutral Ligand on Metal: A Comprehensive Strategy To Mimic Ditopic Ligands in Olefin Polymerization

Synthesis of Modified 4H‐1,2,4‐Benzothiadiazine‐1,1‐dioxides and Determination of their Affinity and Selectivity for Different Types of K_ATP Channels

Guanidin, Kreatin, Kreatinin

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CCCLXXVII.—The condensation of aromatic amino-sulphonic acids with isocyanic acid, phenylcarbimide, and cyanamide

Cited by 4 publications

References 0 publications

H-Bonding Assisted Self-Assembly of Anionic and Neutral Ligand on Metal: A Comprehensive Strategy To Mimic Ditopic Ligands in Olefin Polymerization

H-Bonding Assisted Self-Assembly of Anionic and Neutral Ligand on Metal: A Comprehensive Strategy To Mimic Ditopic Ligands in Olefin Polymerization

Synthesis of Modified 4H‐1,2,4‐Benzothiadiazine‐1,1‐dioxides and Determination of their Affinity and Selectivity for Different Types of KATP Channels

Guanidin, Kreatin, Kreatinin

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Synthesis of Modified 4H‐1,2,4‐Benzothiadiazine‐1,1‐dioxides and Determination of their Affinity and Selectivity for Different Types of K_ATP Channels