Imidazolines derivatives

Imidazole and imidazoline derivatives have provided some useful antimicrobial compounds (Fig. 7). Metronidazole [433-48-1]... 

The ynaminoketones (X = Me) obtained from diacetylene react with 1,2-diaminoethane as simple ynamines by double attack at the triple bond to form imidazoline derivatives 348. 

A rather simple derivative of imidazoimidazoline has been described as an antidepressant agent. Preparation of this compound starts with the displacement of the nitramine grouping in imidazoline derivative by phenyl ethanol amine The product of this reaction is then treated with thio-nyl chloride. The probable chloro intermediate ( ) cyclizes under the reaction conditions to afford imafen (5. ... 

Another imidazoline derivative, lofexidine (71), has different pharmacological properties. 

Pyranopyrroloimidazoles have been prepared stereospecifically by an intramolecular 1,3-dipolar cycloaddition reaction. Either enantiomer of the imidazoline derivative 176 (the -enantiomer is shown) may react with the bromoacetyl-containing acrylate dipolarophile 177, in the presence of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), to give the diastereomerically pure tricyclic product 178 in moderate yield (Equation 15). This reaction involves quaternization of the imidazole N, reaction of the quaternary salt with base to give the 1,3-dipole, which can then react, intramolecularly and stereospecifically, with the tethered dipolarophile <1997TL1647>. 

Aziridines have been synthesized, albeit in low yield, by copper-catalyzed decomposition of ethyl diazoacetate in the presence of an inline 260). It seems that such a carbenoid cyclopropanation reaction has not been realized with other diazo compounds. The recently described preparation of 1,2,3-trisubstituted aziridines by reaction of phenyldiazomethane with N-alkyl aldimines or ketimines in the presence of zinc iodide 261 > most certainly does not proceed through carbenoid intermediates rather, the metal salt serves to activate the imine to nucleophilic attack from the diazo carbon. Replacement of Znl2 by one of the traditional copper catalysts resulted in formation of imidazoline derivatives via an intermediate azomethine ylide261). 

Good yields of imidazoline derivatives have been obtained in the cocyclooligomerization of phenylacetylene with isocyanates and carbodiimides (Scheme 100).166 It has been demonstrated166 by labeling studies in the isocyanate reaction that the hydrogen shift is intramolecular and a mechanism accommodating this feature is illustrated in Scheme 101.166 The final step (85 - 86) in the proposed166 mechanism (Scheme 101) probably occurs via a coordinated acetylene complex and it is notable that related complexes... 

Quite recently [71] an expeditious solvent-free synthesis of imidazoline derivatives, using basic or neutral alumina under microwave irradiation, was reported. The reaction time was reduced from hours to minutes with improved yield compared with conventional heating. 

The imidazoline derivative cibenzohne (64) is a class I antiarrhythmic agent which has undergone clinical tnals in the United States with apparently satisfactory results It is synthesized by diphenylcyclopropananon of acrylonitnle by thermal carbene generation from diphenyldiazo methane (62) to give 1 cyano 2,2 diphenylcyclopropane (63) Reaction of this with ethylenedia mine tosylate completes the synthesis of ciben/oline (64) [221... 

OTC Afrin,Afrin 12-Hour, Ocuclear, Sinex 12 Hour Long-Acting Chemical Class Imidazoline derivative... 

OTC Otrivin Measured-Dose Pump with Moisturizers, Otrivin Nasal Drops, Otrivin Nasal Spray, Otrivin Nasal Spraywith Eucalyptol, Otrivin Nasal Spray with Moisturizers, Otrivin with Measured-Dose Pump Cfiemical Class Imidazoline derivative... 

It is an imidazoline derivative with a partial agonist action. It stimulates presynap-tic, receptors in vasomotor centre of brain... 

The 7 -substituted-2-nitramino-2-imidazoline derivatives were prepd and investigated by McKay et al (Ref 3). Nitration of these products yielded 1 -substituted-2-nitrimino-3-nitroimidazoli-dines, which proved to be stable at room temperature. As examples of these compounds may be cited ... 

Diazadienes have been shown by various groups to be suitable precursors of imidazoline derivatives by means of [4 + 1 ] cycloaddition reactions. In 1976 Matsuda and co-workers were able to cycloadd heterodienes 303, available from AMrimethylsilyl benzophenone imine and phenyl isocyanate, with cyclohexyl isocyanide to obtain 305 in 91% yield, after methanolysis of the initial adduct 304 [76JCS(P1)1523] (Scheme 67). 

The antihypertensive action of clonidine, a 2-imidazoline derivative, was discovered in the course of testing the drug for use as a nasal decongestant. 

Dehydrogenation of A2-imidazolines (416 Z = NR) gives imidazoles, but requires quite high temperatures and a catalyst such as nickel or platinum. Alternatively, hydrogen acceptors such as sulfur or selenium can be used (70AHC( 12)103). A2-Imidazoline derivatives (417) are thermally converted into imidazoles (418) by a retro-Diels-Alder sequence (93JOC3387). 

Phentolamine, an imidazoline derivative, is a potent competitive antagonist at both and 2 receptors (Table 10-1). Phentolamine causes a reduction in peripheral resistance through blockade... 

Approach T (the one-step formation of N(5)-C(6) and C(6)-C(7) bonds) was used only in the study (1996USP5141932) where imidazothienopyridines 282 possessing antitumor activity were synthesized from 2-(3-thienyl)imidazoline derivatives 283. 

Imidazoline derivatives Capsules, ointments, and nasal drops 312... 

Prisinzano T, Dukat M, Law H, et al. 2-(Anilino)imidazolines and 2-(benzyl)-imidazoline derivatives as /z5-HT1D serotonin receptor ligands. Bioorg Med Chem Lett 2004 14 4697-4699. 

Bitumen additives to give wet adhesion to road aggregates Quaternary ammonium compounds Imidazoline derivatives Amine ethoxylates Wetting agents... 

Two major classes of amphoteric surfactants are derived from fatty alkyl hydroxyethyl imidazolines which, in turn, are produced from fatty acids and low molecular weight amines. Because fatty acids are fairly economic, the imidazoline derived amphoacetates tend to be less expensive than the iminodipropionates discussed above. Most imidazoline derived... 

These imidazoline compounds have proved very useful as intermediates to amphoteric surfactants. Products made from them, alkylated with sodium chloroacetate or methyl acrylate were patented by Hans Mannheimer who founded Miranol Company in the USA during the 1950s [2]. Miranol Company became the major vendor of imidazoline derived amphoteric surfactants in the world. Other imidazolines are used to produce amphoteric surfactants, such as alkyl aminoethyl imidazoline, but those products are of less economic significance. 

As mentioned above, most commercial products are based on either a lauric (mainly C-12) or a whole coconut distribution (C-8 to C-18, with approximately 50% C-12) since these alkyl distributions give the best detergency. Early on, the imidazoline derived amphoterics were characterized as exceptionally mild to the skin and eyes relative to most surfactants available at the time. This made them excellent candidates for use in baby shampoos, geriatric cleansing products, hand wash for medical facilities and so on. 

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