Imidazoles 4-chloro

The hexahydropyrrolo[l,2- ]imidazole chloro cycloadducts 57a-c, as a 1/1 mixture of stereoisomers, underwent an elimination on treatment with l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dimethyl sulfoxide (DMSO) at 100°C. It was not possible to isolate the desired dihydropyrroles 58a-c and a second elimination occurred to form the T-substituted pyrroles 59a-c respectively (Scheme 4) <1998J(P1)2061>. 

Clotrimazole. The imidazole derivative clotrimazole (6) was iatroducedia 1969. Clotrimazole [23593-75-1] or l-((9-chloro-a,a-diphenylbenzyl)imidazole is a water-iasoluble antimycotic for topical appHcation, with a broad-spectmm activity against mycoses of the skin and the vagiaa. 

Imidazole, 4-chloro-l-methyl-pK, 5, 384 B-76MI40701, 70AHC(12)103, 80AHC(27)241>... 

Imidazole, 4-methyl-annular tautomerism, 5, 363 association, 5, 362 boiling point, 5, 362 bromination, 5, 398 deuteration, 5, 417 diazo coupling, 5, 403 hydrogen bonding, S, 350 hydroxymethylation, 5, 404 iodination, 5, 400 kinetics, 5, 401 mass spectra, 5, 358 melting point, 5, 362 methylation, 5, 364 sulfonation, 5, 397 synthesis, 5, 479-480, 482, 484, 489 Imidazole, 5-methyl-annular tautomerism, 5, 363 Imidazole, l-methyl-4-chloro-ethylation, 5, 386 Imidazole, l-methyl-5-chloro-ethylation, 5, 386 nitration, 5, 395... 

In 1972, van Leusen, Hoogenboom and Siderius introduced the utility of TosMIC for the synthesis of azoles (pyrroles, oxazoles, imidazoles, thiazoles, etc.) by delivering a C-N-C fragment to polarized double bonds. In addition to the synthesis of 5-phenyloxazole, they also described reaction of TosMIC with /7-nitro- and /7-chloro-benzaldehyde (3) to provide analogous oxazoles 4 in 91% and 57% yield, respectively. Reaction of TosMIC with acid chlorides, anhydrides, or esters leads to oxazoles in which the tosyl group is retained. For example, reaction of acetic anhydride and TosMIC furnish oxazole 5 in 73% yield. ... 

Nafimidone (93), an anticonvulsant compound, also contains an imidazole moiety It seems to have been discovered by accident during a search for antifungal agents Its synthesis is straightforward involving displacement with imidazole of the activated chlorine atom of chloro-methyl-p-naphthylketone (92) [32]... 

N,N -dimethyloxaldiamide is reacted with PCI5 to give 4-chloro-1-methyl imidazole. This is nitrated with HNO3 to give 5-nitro-1-methyl-4-chloroimidazole. Then, a mixture of 4.6 grams of anhydrous 6-mercaptopurine, 5 grams of 1-methyl-4-chloro-5-nitroimidazole and 2.5 grams of anhydrous sodium acetate in 100 ml of dry dimethyl sulfoxide was heated at 100°C for 7 hours. 

Chemical Name 1-[2-[(2-Chloro-3-thienyl)methoxy] -2-(2,4-dichlorophenyl)ethyl] -1 H-imidazole... 

Chemical Name N-(2-Chloro-4-methylphenvl)-4,5-dihvdro-1 H-imidazol-2-amine Common Name —... 

Medium effects were found to be important. A decrease in pH favored more 7-bromination, whereas the proportion of 195 remained fairly constant. Product ratios (Scheme 59) show pH dependence similar to that of imidazole bromination (74AJC2331). In acidic media, both NBS and NIS gave mainly 7-halogeno products (65% and 50 yields, respectively), and NCS gave the 7-chloro along with smaller quantities of 3-, 2,3-, and 3,7-chlorinated species (82CJC3049). 

The reaction of the (necessarily) cis-oxalato complex with HCI in the last example, ensures the c/s-configuration for the chloro complex on recrystallization, the thermodynamically more stable fra s-isomer forms. fra s-Rupy4Cl2 has Ru-N 2.079 A and Ru—Cl 2.405 A. An imidazole complex (imH) tra s-[RuCl4(im)2] shows promise as a tumour inhibitor and is currently undergoing preclinical trials [135]. 

In 2004, Alterman et al. used a microwave-assisted Ullmann-type protocol for the synthesis of N-(f-butyl)-3-[4-(lH-imidazol-l-yl)benzyl]-5-isobutylthiophene-2-sulfonamide (Scheme 106) [61]. Deprotection of the sulfonamide followed by carbamate formation via reaction with butyl chloro-formate finally gave the target compound for biological evaluation as selective angiotensin II AT2 receptor agonist. The IH-imidazole derivative, however, showed only a low affinity for the AT2 receptor (Ki value > 10 p,M). 

CN 2-butyl-4-chloro-l-[[2 -(lH-tetrazol-5-yl)[l,r-biphenyl]-4-yl]methyl]-l//-imidazole-5-methanol monopotassium salt... 

CN 4-chloro-A-(4,5-dihydro-l//-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine... 

C22H22C1N,0 114772-55-3) see Losartan potassium tert-butyl chloroformate (C5H9CIO2 24608-52-4) see Cefalexin 2-butyl-4-chloro-5-hydroxymethyiimidazole (CSII13CIN2O 79047-41-9) see Losartan potassium 2-butyl-4-cbloro-lif-imidazole-5-carboxaldehyde (CnHiiClNjO 83857-96-9) see Eprosartan Losartan potassium... 

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