Benzimidazole sulfones

Petschek [4] used heterocyclic rigid-rod polyionomers, including poly(pyr-idinium) salt, (III), and poly(benzimidazole-sulfonate), (IV), for coating directionally onto charged surfaces to impart planar alignment and pre-tilt to the surfaces. 

On the other hand, some experimental results are in agreement with the predominance of path b (Fig. 24) they arc due in particular to the aptitude of a very large number of substrates to react readily with aldehydes (see references reported for 12 and Ref. 274). Indeed, several successful syntheses of Mannich bases have been carried out starting from the hydroxymethyl derivative of the substrate, as reported for C-Mannich bases obtained from ferrocenyl derivatives,- nitroalkanes. - and hydrogen cyanide as well as for N-, S-, P-Mannich bases of benzimidazoles, sulfonic acids,- phosphines, etc. 

Although it is frequently more convenient to make imidazole and benzimidazole sulfones (and sometimes sulfoxides) by direct oxidation of the thioethers, 4-tosyl groups can also be introduced quite conveniently by a ring synthesis based on the reagent TOSMIC (see Section 4.2 and Scheme 4.2.1). 

Isoamylmethoxy cinnamate (IMC) Ethylhexylmethoxy cinnamate (EHMC) Octocrylene (OCR) Polysilicone 15 (BMP) Benzophenone-3 (B-3) Benzophenone-4 (B-4) Phenyl benzimidazole sulfonic acid (PBSA) 4-Methyl benzyhdene camphor (MBC) Ethylhexyl triazone... 

Chichibabin reaction, 5, 409-410 sulfonation, 5, 429 synthesis, 5, 160, 161, 457-498, 496 tautomerism, 5, 365 toxicity, 1, 139 UV spectra, 5, 356, 357 2H-Benzimidazoles 3,3-dioxides synthesis, 6, 407 2V,7ST-dioxides reactions, 5, 456 Benzimidazoles, aryl-oxidation, 5, 433 Benzimidazoles, nitro-mass spectra, 5, 359 reduction, 5, 441 Benzimidazole-2-sulfonic acids reactions... 

One of the first examples of this type of blend was composed of SPEEK or SPES as the acidic component and diaminated PES, poly(4-vinylpyridine) (P4VP), poly(benzimidazole) (PBl), or poly(ethyleneimine) (PEI) as the basic component. " For blend lEC values of 1.0 meq/g, conductivity values were reported to be good, as was H2/O2 EC performance. Thermal stabilities for these blends was also demonstrated to be high (>270°C). Other examples of acid-base PEMs include blends of SPPO and PBI, sulfonated poly(phthalazinone ether ketone) and aminated SPES, SPIs and aminated Pls, and SPEEK with PES bearing benzimidazole side groups, ° as well as an unusual example in which the blend is composed of sulfonated, hyper-branched polyether and pyridine-functionalized polysulfone. ... 

Asensio, J. A., Borros, S. and Gomez-Romero, P. 2002. Proton-conducting polymers based on benzimidazoles and sulfonated benzimidazoles. Journal of Polymer Science Part A Polymer Chemistry 40 3703-3710. 

Fu, Y. Z., Manthiram, A. and Guiver, M. D. 2006. Blend membranes based on sulfonated poly(ether ether ketone) and polysulfone bearing benzimidazole side groups for proton exchange membrane fuel cells. Electrochemistry... 

Membrane research is a rather diverse field, exploiting perfluorinated iono-mers, hydrocarbon and aromatic polymers, and acid-base polymer complexes. Polyether and polyketo polymers with statistically sulfonated phenylene groups such as sPEK, sPEEK, and sPEEKK or polymers on the basis of benzimidazole have been tested as well. Recent reviews on membrane synthesis and experimental characterization can be found in the literature. ... 

Direct copolymerization of sulfonated monomers has been used to synthesize sulfonated poly (benzimidazoles), poly(benzoxazole)s, and poly(benzothia-zole)s. As an example, Kim et al. synthesized poly-(benzthiazole)s from 2,5-diamino-1,4-benzenedithiol dihydrochloride and either 2-sulfoterethphthalic acid sodium salt, 5-sulfoisophthalic acid sodium salt, or 2,4-disulfoisophthalic acid potassium salt in poly-phosphoric acid (PPA), as shown in Figure 34. Similar sulfonated poly(benzimidazole) and sulfonated poly(benzoxazole) ° structures have also been synthesized. A general synthetic scheme for each is shown in Figure 35. The stability of these polymers in aqueous acidic environments appears... 

Figure 35. Synthesis of sulfonated poly (benzimidazole) and poly(benzoxazole).

The second class of benzo-fused heterocycles accessible from benzofuroxans are benzimidazole oxides. In this case only one carbon from the co-reactant is incorporated in the product. With primary nitroalkanes 2-substituted l-hydroxybenzimidazole-3-oxides (46) are formed via displacement of nitrite, and / -sulfones behave similarly. The nitrile group of a-cyanoacetamides is likewise eliminated to alford 2-amide derivatives (46 R = CONRjX and the corresponding esters are formed in addition to the expected quinoxaline dioxides from acetoacetate esters. Under similar conditions secondary nitroalkyl compounds afford 2,2-disubstituted 2//-benzimidazole-1,3-dioxides (47). Benzimidazoles can also result from reaction of benzofuroxans with phosphorus ylides <86T3631>, nitrones (85H(23)1625>, and diazo compounds <75TL3577>. 

Mit dem Dinatriumsalz von Cyanamid wird 3-Amino-1,2,4-benzotriazin-l,4-bis-oxid (81 %)320 gebildet, mit Cyan-acetamid hingegen 2-Aminocarbony -l-hydroxy-benzimidazol-3-oxid (78%)321 [analog reagieren 1-Nitro-alkane322-324 und (3-Oxo-alkyl)-sulfone]325 ... 

Poly(arylene ether benzimidazole)s have received more attention than any other PAE containing heterocyclic units. This is due primarily to their unique combination of properties even at relatively low molecular weights and their potential for use in several high performance applications. The initial report in 1991 involved polymers from the reaction of 3 different bis[(4-hydroxy-phenyl)benzimidazole]s with various activated aromatic difluoro monomers as shown in Eq. (10) [37]. The bis[(4-hydroxyphenyl)benzimidazole]s were prepared from the reaction of aromatic bis(o-diamines) and phenyl-4-hydroxybenzoate in diphenyl sulfone. The use of 4-hydroxybenzoic acid would obviously reduce the... 

Included in this group of drugs are the benzimidazoles, imidazoUriazoles, tetrahy-dropyrimidines, salicylanilides, substituted phenols, macrocyclic lactones, sulfon-... 

Eight benzimidazoles Animal tissues ACN extn, liq-liq partns, two SPE cleanups 24 Hewlett-Packard RP-18,5 m, with Kontron RP-18 Presat, 25-40 m, guard column O.OIM pentane-sulfonate contg 0.5% TEA, pH 3.5/ACN (50 50) UV 298 nm/ 20-50 ppb/ GC-NPD 39-87% or GC-EI-MS or GC-Pulsed PICI-NICI-MS after derivatization with methyl iodine or pentafluoro- benzyl bromide 358... 

Fig. 29.10.1 Typical chromatograms of a mixed standard working solution (A), a control milk sample (B), and a control milk sample fortified with benzimidazoles at concentrations close to their detection limits (C). Peaks 1, albendazole-2-aminosulfone 2, albendazole sulfoxide 3, oxibendazole 4, oxfendazole 5, albendazole sulfone 6, p-hydroxyfenbendazole 7, albendazole 8, mebendazole 9, fenbendazole sulfone 10, fenbendazole. (From Ref. 343.).

D. 5-Methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl] sulfonyl]-lH-benzimidazole (omeprazole sulfone)... 

The best listing of fungicides that we know of is published annually by the Meister Publishing Company of Willoughby, Ohio in their Farm Chemicals Handbook. They list the following compounds or types of compounds as officially "registered" for use on plants in the United States allyl alcohol, ammonium isobutyrate, antibiotics, benzimidazole types, carbofuran, cadmiums, captan types, coppers, carboxin, dehydroacetic acid, Dexon (sodium [4-(dime thy lamino) phenyl diazo sulfonate), diphenyl,... 

Isothiazoles have also been incorporated into a wide range of established drugs including phenothiazines,123 sulfones,121 sulfonamides,3,66,156 thiosemicarbazones,140,157 amidines,158 nitrohetero-cycles,159 and benzimidazoles,160 but this approach does not appear to have resulted in any major improvements. However, many isothiazoles not directly related to known drugs have biological activity, and representatives are listed in Table I, No attempt has been made to include the numerous patents which mention isothiazole derivatives as part of a series, but for which no special claims are made. 

Tetradifon halogenated aromatic, sulfone Tetramethrin pyrethroid Tetrasul halogenated aromatic o,o,o, o -Tetrapropyl dithiopyrophosphate phosphoro organic, thiopyrophosphate Thenylchlon amide, heterocyclic sulfur, thiophene Thiabendazole heterocyclic nitrogen, benzimidazole, thiazole... 

PB PBI PBMA PBO PBT(H) PBTP PC PCHMA PCTFE PDAP PDMS PE PEHD PELD PEMD PEC PEEK PEG PEI PEK PEN PEO PES PET PF PI PIB PMA PMMA PMI PMP POB POM PP PPE PPP PPPE PPQ PPS PPSU PS PSU PTFE PTMT PU PUR Poly(n.butylene) Poly(benzimidazole) Poly(n.butyl methacrylate) Poly(benzoxazole) Poly(benzthiazole) Poly(butylene glycol terephthalate) Polycarbonate Poly(cyclohexyl methacrylate) Poly(chloro-trifluoro ethylene) Poly(diallyl phthalate) Poly(dimethyl siloxane) Polyethylene High density polyethylene Low density polyethylene Medium density polyethylene Chlorinated polyethylene Poly-ether-ether ketone poly(ethylene glycol) Poly-ether-imide Poly-ether ketone Poly(ethylene-2,6-naphthalene dicarboxylate) Poly(ethylene oxide) Poly-ether sulfone Poly(ethylene terephthalate) Phenol formaldehyde resin Polyimide Polyisobutylene Poly(methyl acrylate) Poly(methyl methacrylate) Poly(methacryl imide) Poly(methylpentene) Poly(hydroxy-benzoate) Polyoxymethylene = polyacetal = polyformaldehyde Polypropylene Poly (2,6-dimethyl-l,4-phenylene ether) = Poly(phenylene oxide) Polyp araphenylene Poly(2,6-diphenyl-l,4-phenylene ether) Poly(phenyl quinoxaline) Polyphenylene sulfide, polysulfide Polyphenylene sulfone Polystyrene Polysulfone Poly(tetrafluoroethylene) Poly(tetramethylene terephthalate) Polyurethane Polyurethane rubber... 

Azolesulfonic acids frequently exist as zwitterions. The usual derivatives are formed, e.g., pyrazole-3-, -4-, and -S-sulfonic acids all give sulfonyl chlorides with PCI5. The sulfonic acid groups can be replaced by nucleophiles under more or less vigorous conditions, e.g., by hydroxy in imidazole-4-sulfonic acids at 170C, and by hydroxy or amino in thiazole-2-sulfonic acids. Benzimidazole-2-sulfonic acids react similarly. 

Benzimidazole-containing sulfonated polyimides, (IV), prepared by Bmnelle [4] were effective as proton exchange membranes for fuel cells. 

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