- Base-promoted annulation of amidoximes with alkynes: Simple access to 2,4-disubstituted imidazoles
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An efficient construction of imidazole ring by a Cs2CO3-promoied annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synehetic ropte with high atom-utilieation for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Intornal alkynes can also undetgo the annulation to give 2,4,5-trisubstituted imidazoles.
- Hua, Ruimao,Iqbal, Muhammad Asif,Lu, Le,Mehmood, Hina
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- Modular Synthesis of Di- A nd Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors
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A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.
- De Toledo, Ian,Grigolo, Thiago A.,Bennett, James M.,Elkins, Jonathan M.,Pilli, Ronaldo A.
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p. 14187 - 14201
(2019/10/16)
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- ZnCl2-Catalyzed [3 + 2] Cycloaddition of Benzimidates and 2 H-Azirines for the Synthesis of Imidazoles
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ZnCl2-catalyzed [3 + 2] cycloaddition reaction of benzimidates and 2H-azirines has been developed. This convenient method allowed the efficient construction of a series of multisubstituted imidazoles in moderate to good yields under mild reaction conditions. This transformation exhibits good reactivity and high functional group tolerance.
- Shi, Shoujie,Xu, Kang,Jiang, Cheng,Ding, Zhenhua
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p. 14791 - 14796
(2018/11/23)
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- One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes
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Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.
- Yamamoto, Takahiro,Togo, Hideo
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p. 4187 - 4196
(2018/08/21)
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- Copper-Catalyzed Simultaneous Activation of C-H and N-H Bonds: Three-Component One-Pot Cascade Synthesis of Multi?-substituted Imidazoles
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A copper-catalyzed expedient, practical, and straightforward approach for the one-pot three-component modular synthesis of multisubstituted imidazoles has been described by using arylacetic acids, N -arylbenzamidines, and nitroalkanes. The reaction involv
- Pardeshi, Sachin D.,Sathe, Pratima A.,Vadagaonkar, Kamlesh S.,Melone, Lucio,Chaskar, Atul C.
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p. 361 - 370
(2018/01/12)
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- One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using N-Bromosuccinimide
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N-bromosuccinimide (NBS)-mediated one-pot, green, efficient and practical synthesis of substituted imidazoles and quinoxalines has been achieved by the reaction of styrenes with N-arylbenzamidines and o-phenylenediamines, respectively, in a water:1,4-dioxane mixture. The reaction involves formation of an α-bromo ketone as an intermediate in the presence of NBS and water, followed by condensation with the N-arylbenzamidine and o-phenylenediamine. Use of an inexpensive NBS as a bromine source as well as an oxidant, water as a solvent and readily available starting materials makes this protocol environmentally benign and economically viable. Substituted imidazoles and quinoxalines were obtained in good to excellent yields with wide functional group compatibility. (Figure presented.).
- Pardeshi, Sachin D.,Sathe, Pratima A.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
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supporting information
p. 4217 - 4226
(2017/12/07)
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- Imidazoles from nitroallylic acetates and α-bromonitroalkenes with amidines: Synthesis and trypanocidal activity studies
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Cascade reactions of amidines with nitroallylic acetates and α-bromonitroalkenes provide potentially bioactive imidazoles in good to excellent yields in most cases. While 2,4-disubstituted imidazol-5-yl acetates are formed in the first case, 2,4-disubstituted imidazoles, bearing no substituent at position 5, are the products in the second case. These two series of imidazoles, viz. 2,4,5-trisubstituted and 2,4-disubstituted, were screened for their activity against the protozoan parasite Trypanosoma cruzi which is responsible for Chagas disease. As many as three compounds were as active as the standard benznidazole and two others were 2-3-fold more active highlighting the potential of substituted imidazoles, easily accessible from nitroalkenes, as possible anti-parasitic agents.
- Gopi, Elumalai,Kumar, Tarun,Menna-Barreto, Rubem F. S.,Valen?a, Wagner O.,Da Silva Júnior, Eufranio N.,Namboothiri, Irishi N. N.
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p. 9862 - 9871
(2015/10/05)
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- Hypervalent iodine in synthesis 81: A one-pot procedure for the synthesis of 1H-imidazole derivatives by cyclocondensation of ketones with [Hydroxy(tosyloxy)iodo]benzene and amidines
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Tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB), followed by treatment with amidines provides a one-pot procedure for the synthesis of 1H-imidazole derivatives with good yields.
- Zhang,Chen
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p. 2075 - 2077
(2007/10/03)
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- METHOD OF TREATING CONDITIONS SUSCEPTIBLE TO MODULATION OF NPY RECEPTORS WITH DIARYLIMIDAZOLE DERIVATIVES
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Certain diaryl imidazoles act as partial agonists or antagonists for NPY receptors, in particular NPY 5 receptors. They are of use, for example in treating loss of appetite. Such compounds bear aryl groups in the 2 position. Many of the compounds are novel.
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- SYNTHESIS OF IMIDAZOLE DERIVATIVES FROM α-HALOOXIMES AND AMIDINES BY USE OF IRON CARBONYLS
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The reaction of α-halooximes with amidines in the presence of iron carbonyls gives imidazole derivatives in good yields.This reaction occurs via deoxygenation of 4H-1,2,5-oxadiazines by iron carbonyls.
- Nakanishi, Saburo,Nantaku, Junji,Otsuji, Yoshio
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p. 341 - 342
(2007/10/02)
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