2-Imidazolines, synthesis

By analogous fashion to imidazoline synthesis (Section 1.11.4.2.2), oxazolines have been introduced by modification of an acrylonitrile-containing polymer with ethanolamine (75JAP(K)75160392). In another modification (Scheme 99), chloromethylated polystyrene) (192) was treated with a Iithiated oxazoline (207) derived from reaction of 2-methyloxazo-Iine and butyllithium (78MI11106). The oxazoline groups were incorporated, in this study, as intermediates to carboxyl groups. 

Ramalingam, B., Neuburger, M., Pfaltz, A. 2007. Synthesis of chiral C-2-symmetric methylene- and boron-bridged bis(imidazolines). Synthesis Stuttgart (4) 572-582. 

S. Bontemps, J. S. Quesnel, K. Worrall, B. A. Amdtsen, Angew. Chem. Int. Ed 2011, 50, 8948-8951. Palladium-catalyzed aryl iodide carbonylation as a route to imidazoline synthesis design of a five-component coupling reaction. 

Imidazolidin-2-one, l-(5-nitro-2-thiazolyl)-pharmacological activity, 6, 328 Imidazolidin-4-one, l-aryl-3-phenyl-2-thioxo- C NM S, 355 Imidazolidinones C NMR, 5, 355 Imidazolidin-2-ones nucleophilic displacement, 5, 428 polymers, 1, 279-280 reactivity, 5, 376 synthesis, 5, 466, 471 Imidazolidin-4-ones synthesis, 5, 468 Imidazoline, 2-alkyl-synthesis, 5, 463 Imidazoline, 2-amino-applications, 5, 498 Imidazoline, 2-aryl-synthesis, 5, 463 Imidazoline, 2-methyl-synthesis, 5, 487 Imidazoline, 2-nitroamino-synthesis, 5, 471 2-Imidazoline, 2-arylamino-tautomerism, 5, 368 2-Imidazoline, 1-benzyl-methylation, 5, 425 2-Imidazoline, 1,2-diaryl-synthesis, 5, 463... 

S-group removal from, S, 445 oxidation, S, 445 reactions, S, 443-445 reactivity, 5, 375-376 synthesis, S, 493 Imidazoline-2-thiones Mannich reaction, 5, 405 reactions, 5, 102, 443-444 with alkynes, 5, 444 synthesis, S, 493... 

Imidazolinium perchlorate, 4-hydroxy-2,5,5-trimethyl-4-phenyl-synthesis, S, 487 Imidazolinium salts antistatic agents, 1, 409 Imidazolinium salts, 1-vinyl-polymerization, 1, 280 Imidazolin-2-one, 1-cyano-synthesis, S, 482 Imidazolin-2-one, 4,5-dialkyl-synthesis, S, 491 Imidazolin-2-one, 4,5-diaryl-bromination, S, 399-400 lmidazolin-2-one, 4,5-di( p-bromophenyl)-reactions... 

Imidazolin-5-one, 2-methyl- H NMI 5, 354 2-Imidazolin-5-one, 2-phenyl-reactivity, 5, 376 synthesis, 5, 479... 

Imidazolin-2-one, 1,5-diphenyl-4-aryl-synthesis, 5, 492 4-Imidazolin-2-one, 1-hydroxy-synthesis, 5, 474—475 4-Imidazolin-2-one, l-methyl-3-phenyl- C NMR, 5, 355 Imidazolinones acylation, 5, 424, 443 alkylation, 5, 443 developers... 

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

Quatemized imidazolines with an amido moiety are suitable formulations for general oil and gas field applications. The synthesis of such compounds is detailed in the literature [1218]. For aqueous systems that contain sulfide compounds, a mixture has been described [262] that consists of an aqueous solution of an alcohol such as diethylene glycol monobutyl ether, butyl cellosolve, additional orthophosphoric acid, a fatty acid (from tall oil), substituted imidazoline, an ethoxylated fatty diamine (polyamines such as ethylenediamine, diethylenetriamine, etc.), and a molybdate compound. 

Imidazolines are also formed in silver cyanide-catalyzed cyclization of alkyl isocyanides with aliphatic diamines (Scheme 103).169 This simple synthesis can be applied in a general way with difunctional nucleophiles and has been used to prepare benzimidazoles, oxazoles, thiazoles, and oxazines.169 It is suggested that transient carbene complexes are formed in these reactions (cf. 87 in Scheme 103) but further work is required to ascertain the mechanism and scope of these processes. 

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. 

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