Tetra imidazoline

Filtrate A was extracted with ether, dried, acidified with alcoholic hydrogen chloride, and the salt which separated was collected end dried. There was thus obtained, when all the salt had been combined, 250 grams (69.3% of the theoretical yield) of 2-( 1,2,3,4-tetra-hydro-1-naphthyl)imidazoline hydrochloride, melting at 256° to 257°C. 

Thermolysis of a stable radical 4-[(hydroxyimino)nitromethyl]-2,2,5,5-tetra-methyl-3-imidazolin-l-oxyl 13 gives the corresponding spin-labeled nitrile oxide. It was also identified in isoxazolines formed in cycloadditions with olefins (88). 

Methylated 1,4-dihydropyrazines (1,2,4-tri-, 1,2,4,5-tetra-, and 1,2,4,6-tetramethyl) as well as imidazolines have been isolated from the reaction of sucrose with methylamine at high temperatures (120°-260°), for prolonged reaction periods (18 hours) and in the presence of ammonium phosphate as catalyst. 1,4-Dihydropyrazines are also isolated from the reaction of sucrose and ethanolamine sucrose-ammonia interaction yields a wide range of pyrazines and imidazoles.369-372... 

Treatment of the long-chain imidazolium salts 263 with potassium, sodium, and tetra-n-butylammonium borohydrides affords the acyclic diamines 264 and 265. The isomer ratio was not reported. Sodium cyanobo-rohydride failed to reduce the same salt under a variety of conditions. The imidazoline 266 reacts with LAH in THF above — 10°C to give the 1,2-di-aminoethane 267. Sodium borohydride is a less effective reducing agent in this reaction, achieving the same conversion over a longer period of time. Other less reactive hydrides [LiBH4, NaBHjCN, LiAlH(0-t-Bu)j] do not react. 

The thiazole ring of the 5-(D-arahfno-tetritol-l-yl)-imidazo[2,l-6]thiazol-ium olate 160 was assembled onto the imidazole ring of 4-(tetra-0-acetyl-D-flrabino-tetritol-l-yl)imidazoline-2-thione (156) by reaction with 2-bromophenylacetic acid (91MI7) (Scheme 47). 

The chloro(ethoxycarbonyl)iminium chloride Et02CCl=NHMe CE is a versatile intermediate for the synthesis of heterocycles with phenylurea, for example, it affords the imidazolinedione (409). Treatment of the complex azine (CF3)2C=N—C(NMe2)=N—N=C(CF3)2 with t-butyl isocyanide yields the imidazoline derivative (410). Mixtures of meso- and DL-tetra-arylimidazolidinethiones (411) are obtained by successive treatment of Schiffs bases Ar CH=NAr with sodium and carbon disulphide.The acid-catalysed... 

The N -allyloxy-carbonyl derivative of 2-methyl-(l,2-dideoxy-a-D-gluco-pyrano)[2,l-d]-l-imidazolines, inhibitors of /1-N-acetylglucosaminidases, have been formed as a byproduct during a study on tetra-O-acetyl-2-allyloxy-2-carbonylamino-)S-D-glucose synthesized as a glycosyl donor and when no available acceptor was present in the reaction media of acetonitril in the presence of trimethysilyl triflate it formed almost quantitatively [78,79). 

Polymerization of tetramethylammonium methacrylate was carried out in water at 45 °C in the presence of the water soluble dithiobenzoate RAFT agent 18 and with 2,2 -azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (Wako VA-044) initiator. Methylation of the resultant poly(tetra-methylammonium methacrylate) with excess methyl iodide provided PMMA with Mn 8200, Mw/A/nl.l7 and/nm.-/nr.-rr 2 21 77 compared to poly(methacrylic add) under similar conditions with mm.mrrr 3 34 63 (this is similar to PMMA obtained by bulk polymerization for which mm.mrrr 3 35 62). Polymerization of salts (Na, K, Cs) methacrylic acid with inorganic counterions also gave a more syndiotactic polymer though the effect appears smaller... 

Other reactions that involved [Mn(TNH2PP)Cl MWCNT] as catalytic nanoreactor are the oxidation with sodium periodate of 2-imidazolines in MeCN [174] and the oxidative decarboxylation of a-arylcarboxylic acids with sodium periodate [175] (Scheme 14.8 a,b). On the other hand, iron(lll) me o-tetra(2-chlorophenyl)porphyrin, coordinated to hydroxyl-functionalyzed MWCNTs, catalyzed the oxidation of alkanes, alkenes, and sulfides using tetrabutylammo-nium peroxomonosulfate (BU4NHSO5) as oxygen source [176] (Scheme 14.8c). 

Phenyl-4,5-(D- / cero-L- /Mco-heptofurano)imidazolidine-2-thione, -p-tolyl-4-(j8-D-erythrofuranosyl)imidazoline-2-thione, 2,3-diphenyl-5-(a-D-lyxo-furanosyl)tetrazolium bromide, l-(2,3,4,6-tetra-0-acetyl-a-D-mannopyrano-syl)-A, A -dimethylisocyanuric acid. ... 

The fructofurano-oxazoline 16 was obtained by reaction of 1,6-di-O-trityl-D-fructosc with cyanamide, and used in the construction of nucleoside analogues (see Chapter 20). The imidazoline 17 formed through solvent incorporation when l,3,4,6-tetra-0-acetyl-2-allyloxycarbonylamino-2-deoxy- 3-D-glucose was used as a glycosylating agent in acetonitrile. Synthesis of the cross-conjugated betaines 18 from glucosylamine has been reported. ... 

Imidazolidine and imidazoline derivatives were formed when dialdose derivatives reacted with 2,3-bis(hydroxylamino)-2,3-dimethylbutane (Scheme 60) oxidation of these derivatives afforded stable free radicals that were examined by e.s.r. spectroscopy. Several oxazole and thiazolidine derivatives having C-5 and C-6 of 3-0-benzyl-l,2-0-isopropylidene-jS-L-idofuranose as part of the heterocyclic ring, and a new class of bicyclic thiazolidine derivative (172) have been prepared by the reactions shown in Scheme 61. The bis(l,3,4-oxadia-zole) derivative (173) has been prepared by condensative cyclization of 2,3,4,5-tetra-O-acetylgalactaric acid bis(benzoylhydrazide) with triethyl orthoformate in p-dioxan. Other heterocyclic derivatives are referred to in Chapters 14 and 15. 

A stirred mixture of l-(o-nitrophenethyl)-2-methylmercapto-2-imidazoline hydrio-dide and Zn-dust in aq. 50%-acetic acid heated 3.5 hrs. at 90° 2,3 5,6-tetra-... 

Oxidation of 1-hydroxy derivatives (6a-g) with lead dioxide in nonpolar organic solvents leads smoothly to nitroxides, namely 2,2,5,5-tetra-alkyl-3-imidazoline-3-oxide-l-oxyls (7a-g) (Volodarsky and Kutikova, 1971). In the crystalline state radicals 7 can be stored for a long time without decomposition. Both radical precursors 6 and the radicals themselves enter into various substitution, condensation, and other reactions. 

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