Boron Heterocycles Bearing a Peripheral Resemblance to Naturally-Occurring Purines: Design, Syntheses, Structures, and Properties

Groziak, Michael P.; Ganguly, Anusree; Robinson, Paul D.

doi:10.1021/ja00096a017

Cited by 78 publications

(66 citation statements)

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“…Schiff bases are versatile intermediates in organic synthesis and have been used to prepare numerous pharmacologically important compounds [16][17][18][19][20]. In this study, we have found that sulfanilamide derivatives add to salicylaldehyde to give compounds having spectroscopic data consistent with the salicylaldimines (a-g) (Scheme 1), where addition occurs at the more nucleophilic NH 2 group in cases containing two primary amine groups (a-c).…”

Section: Sulfanilamidesmentioning

confidence: 82%

Palladium(II) Schiff base complexes derived from sulfanilamides and aminobenzothiazoles

Coombs

Ringer

Blacquiere

et al. 2005

Transition Met Chem

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Schiff bases (HL) derived from sulfanilamides or aminobenzothiazoles add to Pd(OAc) 2 to give complexes of the type PdL 2 (1-7) in moderate to excellent yields. Reactions of Schiff bases containing pyrimidine groups, however, gave several products arising from competing coordination of the pyrimidine nitrogen. Palladium complexes and Schiff bases have been investigated as antifungal agents against Aspergillus niger and Aspergillus flavus.

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Section: Sulfanilamidesmentioning

confidence: 82%

Palladium(II) Schiff base complexes derived from sulfanilamides and aminobenzothiazoles

Coombs

Ringer

Blacquiere

et al. 2005

Transition Met Chem

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“…These results suggest the intermolecular reactions between boronic acid groups and imines of PABA in acetonitrile independent of the oxidation state of the polymer. For example, the dimer of 2-aminophenylboronic acid in aprotic solvent [35] and self-crosslinked self-doped PABA [22] in the solid state exist as six-member heterocyclic complexes containing a boron-imine dative bond. The intermolecular reactions between boronic acid groups and imines in PABA in acetonitrile are further supported by UV-vis, PM-IRRAS and XPS spectroscopic measurements.…”

Section: Resultsmentioning

confidence: 99%

“…These results suggest that the bipolarons are present in the PABA nanostructured films throughout applied potential range of À0.6 to 1.0 V, presumably due to anionic cross-linked sites, stable in aprotic solvent, and consisting of sixmember heterocyclic complexes containing a boron-imine dative bond. [35] In so doing, a self-doped, cross-linked conducting PABA is likely formed. In the case of PABA nanostructured films prepared and after precipitation and purification, re-dispersed in methanol ( Figure 8C), the spectral transformations from leucoemeraldine to pernigraniline state are significant with applied potential in acetonitrile with 1 M LiClO 4 .…”

Section: Resultsmentioning

confidence: 99%

Conducting Poly(anilineboronic acid) Nanostructures: Controlled Synthesis and Characterization

Deore¹,

Yu²,

Woodmass³

et al. 2008

Macro Chemistry & Physics

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Self‐doped poly(anilineboronic acid) (PABA) nanostructures have been prepared by chemical polymerization in an aqueous acid solution and aliphatic alcohols. In aliphatic alcohols, PABA is soluble under the polymerization conditions. According to 11B NMR studies, the formation of anionic tetrahedral boronate ester in aliphatic alcohols in the presence of fluoride forms the basis of self‐doped, soluble PABA. Transmission electron microscope images show the formation of nanostructures with different shapes and forms in different solvents after precipitation of the polymer as a result of ion exchange in the presence of 0.5 M HCl. The spectroscopic and cyclic voltammetric results confirm the formation of conducting PABA nanostructures in high yield. The conductivity of PABA thin films made from the nanostructures prepared in aqueous acid, methanol, ethanol and 1‐propanol is approximately 15 and 3.0, 2.1 and 1.9 S · cm−1, respectively. The conducting PABA nanostructures are processable since they are easily re‐dispersed in the various solvents up to approximately 5 mg · mL−1. UV‐vis kinetic measurements, XPS and 11B NMR results suggest that the formation of various nanostructures is influenced by the polymerization rate, the degree of self‐doping versus external doping, and the polarity of the solvents used. The PABA nanostructured films produced from these structures exhibit enhanced redox stability in a wider potential window in non‐aqueous media compared to polyaniline due to formation of six‐member heterocyclic complexes containing a boron‐imine dative bond resulting in a self‐doped self‐cross‐linked polymer. The degree of crosslinking depends on the nature of nanostructures. In non‐aqueous media, the self‐doped, self‐cross‐linked PABA nanostructured films are much less susceptible to cathodic and anodic degradation at extreme potentials, overcoming a major limitation of more common conducting polymers.magnified image

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“…We had hoped to find an ␣-substituted b-ureidoboronic ester 10 that could cyclize to an intermediate 11 and undergo H-X elimination to provide the boron analog of uracil 12, which would be of interest as a possible anticancer, antiviral, or 10 Bneutron capture cancer therapy agent [8]. All attempts at further elaboration of 6 and 7 in this direction failed to yield products that could be purified.…”

Section: Results and Discussion [[Bis(trialkylsilyl)amino]methyl]boromentioning

confidence: 99%

An Exploratory Study of Silylated Amino Boronic Ester Chemistry

et al. 1997

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Boron Heterocycles Bearing a Peripheral Resemblance to Naturally-Occurring Purines: Design, Syntheses, Structures, and Properties

Cited by 78 publications

References 0 publications

Palladium(II) Schiff base complexes derived from sulfanilamides and aminobenzothiazoles

Palladium(II) Schiff base complexes derived from sulfanilamides and aminobenzothiazoles

Conducting Poly(anilineboronic acid) Nanostructures: Controlled Synthesis and Characterization

An Exploratory Study of Silylated Amino Boronic Ester Chemistry

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