On the basic hydrolysis of disubstituted isocyanurates

Argabright, P. A.; Phillips, Brian L.

doi:10.1002/jhet.5570070449

Cited by 7 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Argabright and coworkers [13] prepared N.N-disubstituted isocyanurates by channeling in NC0 9 ions into polymerizations in DMF at elevated temperatures. We did not observe such a reaction with solid KNCOand Aliquat 336.…”

Section: Influence Of Catalystsmentioning

confidence: 99%

“…Beside diphenylurea, a compound was isolated that showed mp 258-259°C, a mass spectroscopic molecular peak at m]e = 255 (=C1JfI3N302)' and IR bands characteristic ofNH and amide residues. It turned out to be the known [14,15] 1,5-diphenylbiuret «N-phenyl-N'-(phenylcarbomoyl)urea) 4 (one lit. mp is 254-255°C [14], others vary [15]).…”

Section: Influence Of Catalystsmentioning

confidence: 99%

“…It turned out to be the known [14,15] 1,5-diphenylbiuret «N-phenyl-N'-(phenylcarbomoyl)urea) 4 (one lit. mp is 254-255°C [14], others vary [15]). Argabright and Phillips [15] have shown that 4 can be formed by hydrolysis of 5, but in our case a more direct path to 4 cannot be ruled out.…”

Section: Influence Of Catalystsmentioning

confidence: 99%

“…mp is 254-255°C [14], others vary [15]). Argabright and Phillips [15] have shown that 4 can be formed by hydrolysis of 5, but in our case a more direct path to 4 cannot be ruled out. The above results show that phase transfer catalysis is the most effective means to bring about isocyanate trimerizations.…”

Section: Influence Of Catalystsmentioning

confidence: 99%

See 3 more Smart Citations

Onium Salt Catalyzed Preparation of Isocyanurates (Applications of Phase Transfer Catalysis, Part 28 [1])

Broda

Dehmlow

Schulz

1985

Israel Journal of Chemistry

View full text Add to dashboard Cite

show abstract

Section: Influence Of Catalystsmentioning

confidence: 99%

Section: Influence Of Catalystsmentioning

confidence: 99%

Section: Influence Of Catalystsmentioning

confidence: 99%

Section: Influence Of Catalystsmentioning

confidence: 99%

See 2 more Smart Citations

Onium Salt Catalyzed Preparation of Isocyanurates (Applications of Phase Transfer Catalysis, Part 28 [1])

Broda

Dehmlow

Schulz

1985

Israel Journal of Chemistry

View full text Add to dashboard Cite

show abstract

“…Under these conditions the reaction took place smoothly, to give a 90% of conversion after 3 hours, affording the expected N-phenyl-N¢-(pyridin-2-yl)urea (3a) in relatively good isolated yield (78%). Trace amounts of aniline (4), N,N¢-diphenylurea (5), 1,5-diphenylbiuret (6) 19 and N-phenyl-N¢-(pyridin-2-yl)amine (7a) 20 were observed as side-products (Scheme 1), the amounts of which strongly depended on the reaction times. Increasing the reaction times in order to achieve a complete conversion of the reactants did not lead to a higher yield of isolated 3a, but resulted in a significant increase of all of the side-products formed in the reaction.…”

mentioning

confidence: 97%

Regioselective Preparation of Pyridin-2-yl Ureas from 2-Chloropyridines Catalyzed by Pd(0)

Abad¹,

Agulló²,

Cuñat³

et al. 2005

Synthesis

View full text Add to dashboard Cite

The palladium-catalyzed ureidation reaction of 2-chloropyridines can be regioselectively performed in good yield, with both aryl and aliphatic ureas, using xantphos as the ligand, Pd(OAc) 2 as the source of palladium, NaOt-Bu/H 2 O or NaOH/H 2 O as the base, and dioxane as the solvent The pyridinyl ureido moiety constitutes a structural motif common to several classes of ureas of great interest in the pharmacologic, agronomic and new material fields. 1 Much interest has been recently paid to pyridin-2-yl ureas, which due to the particular disposition of their ureido and pyridine groups are able to participate in specific hydrogen bonding patterns that control their physical and biological properties. Recent examples include pyridin-2-yl ureas with anticancer properties, a new class of potent Cdk4 inhibitors, 2 strong receptors for cytosine, with potential use as DNA binders, 3 a new type of low molecularweight gelators, with great potential for functional materials, 4 and pyridin-2-yl-based photodegradable polymers, potentially useful in the field of micro/nanolithography. 5In general, conventional procedures for the preparation of pyridinyl ureas involve the use of toxic and troublesome reagents such as isocyanates, phosgene or CO 2 . [2][3][4][5]6 In spite of the large amount of research work that has been done on the palladium-catalyzed C-N bond forming reactions of aryl/heteroaryl systems (e.g. amine, 7 amide, 8 imine, 9 carbamate, 10 lactam, 11 sulphonamide, 8 and sulfoximines 12 arylations have been described), only a few examples of palladium-catalyzed arylation of ureas have been reported recently. These include the cross-coupling of urea and phenylurea with activated 13 and unactivated 14 aryl bromides and iodides, the coupling of an aryl bromide with cyclic ureas, 8 and some intramolecular palladium-catalyzed arylation of ureas. 15 To the best of our knowledge, the analogous cross-coupling reaction of heteroaryl halides, and in particular of the generally less reactive chlorides, has not been explored. 16 In relation to our interest in the preparation of pyridinyl ureas, 17 we have investigated the viability of the palladium-catalyzed coupling of readily available chloropyridines with several types of ureas. We show that 2-chloropyridines can react efficiently with both aryl and alkyl ureas, allowing the preparation of both N-phenyland N-alkyl-N¢-pyridin-2-yl ureas in good to excellent yields. 18 Initially, we examined the cross-coupling of 2-chloropyridine (1a) with phenylurea (2) under the conditions previously described by Beletskaya 13,14 for the related coupling of aryl bromides with the same urea (Table 1, entry 1). Under these conditions the reaction took place smoothly, to give a 90% of conversion after 3 hours, affording the expected N-phenyl-N¢-(pyridin-2-yl)urea (3a) in relatively good isolated yield (78%). Trace amounts of aniline (4), N,N¢-diphenylurea (5), 1,5-diphenylbiuret (6) 19 and N-phenyl-N¢-(pyridin-2-yl)amine (7a) 20 were observed as side-products (Scheme 1), the amounts of which s...

show abstract

ChemInform Abstract: BASISCHE HYDROLYSE DISUBSTITUIERTER ISOCYANURATE

Argabright¹,

Phillips²

1970

Chemischer Informationsdienst. Organische Chemie

View full text Add to dashboard Cite

On the basic hydrolysis of disubstituted isocyanurates

Cited by 7 publications

References 0 publications

Onium Salt Catalyzed Preparation of Isocyanurates (Applications of Phase Transfer Catalysis, Part 28 [1])

Onium Salt Catalyzed Preparation of Isocyanurates (Applications of Phase Transfer Catalysis, Part 28 [1])

Regioselective Preparation of Pyridin-2-yl Ureas from 2-Chloropyridines Catalyzed by Pd(0)

ChemInform Abstract: BASISCHE HYDROLYSE DISUBSTITUIERTER ISOCYANURATE

Contact Info

Product

Resources

About