cas 670-83-7, 2,4-Diphenylimidazole | Articles data

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Structure-activity relationship studies on 2-heteroaryl-4-arylimidazoles NPY5 receptor antagonists
A series of 2-heteroaryl-4-arylimidazoles with potent in vitro activity at the NPY5 receptor was developed. Introduction of electron-withdrawing groups on the 4-aryl ring led to a significant improvement of in vitro potency. Several analogues from this series had anorectic activity in rodent feeding models, but were also found to have undesired behavioral effects in spontaneous locomotor activity.
Elliott, Richard L.,Oliver, Robert M.,LaFlamme, Janet A.,Gillaspy, Melissa L.,Hammond, Marlys,Hank, Richard F.,Maurer, Tristan S.,Baker, Demetria L.,DaSilva-Jardine, Paul A.,Stevenson, Ralph W.,Mack, Christine M.,Cassella, James V.
p. 3593 - 3596
(2003)
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Base-promoted annulation of amidoximes with alkynes: Simple access to 2,4-disubstituted imidazoles
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
(2020/09/17)

Nickel-Catalyzed Construction of 2,4-Disubstituted Imidazoles via C–C Coupling and C?N Condensation Cascade Reactions
A convenient Ni(II)-catalyzed C?C and C?N cascade coupling reaction was developed to directly access various 2,4-disubstituted imidazoles. The reaction scope covers a variety of aryl and aliphatic substitutions, which demonstrate moderate-to-excellent yie
Fang, Shengyang,Yu, Haihua,Yang, Xicheng,Li, Jianqi,Shao, Liming
supporting information
p. 3312 - 3317
(2019/06/13)

Structure and Reactivity of Highly Twisted N-Acylimidazoles
A modular and efficient synthesis of highly twisted N-acylimidazoles is reported. These twist amides were characterized via X-ray crystallography, NMR spectroscopy, IR spectroscopy, and DFT calculations. Modification of the substituent proximal to the amide revealed a maximum torsional angle of 88.6° in the solid state, which may be the most twisted amide reported for a nonbicyclic system to date. Reactivity and stability studies indicate that these twisted N-acylimidazoles may be valuable, namely as acyl transfer reagents.
Stone, Elizabeth A.,Mercado, Brandon Q.,Miller, Scott J.
supporting information
p. 2346 - 2351
(2019/04/10)

Rh-Catalyzed Annulation of ortho-C?H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-c]quinazolines
A Rh-catalyzed unique and direct approach for constructing a series of 5-arylimidazo[1,2-c]quinazolines in moderate to excellent yields from simple and readily available 2-arylimidazoles and 3-phenyl-1,4,2-dioxazol-5-ones was described. This procedure pro
Wu, Xiaopeng,Sun, Song,Xu, Shengbo,Cheng, Jiang
supporting information
p. 1111 - 1115
(2018/01/27)

ZnCl2-Catalyzed [3 + 2] Cycloaddition of Benzimidates and 2 H-Azirines for the Synthesis of Imidazoles
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
p. 14791 - 14796
(2018/11/23)

Visible Light as a Sole Requirement for Intramolecular C(sp3)-H Imination
A novel, simple, and practical visible-light-mediated intramolecular α-C(sp3)-H imination of tertiary aliphatic amines containing β-O-aryl oximes leading to N-heterocycles has been developed. The reaction was performed well at rt with tolerance of some functional groups. Importantly, the selective C-H functionalization did not require added catalyst, oxidant, additive, acid, and base; visible light was the sole requirement.
Li, Jingjing,Zhang, Pengxiang,Jiang, Min,Yang, Haijun,Zhao, Yufen,Fu, Hua
p. 1994 - 1997
(2017/04/28)

One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using N-Bromosuccinimide
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.
supporting information
p. 4217 - 4226
(2017/12/07)

IEDDA Reaction of the Molecular Iodine-Catalyzed Synthesis of 1,3,5-Triazines via Functionalization of the sp3 C-H Bond of Acetophenones with Amidines: An Experimental Investigation and DFT Study
The present work reports an inverse electron demand Diels-Alder (iEDDA)-type reaction to synthesize 1,3,5-trizines from acetophenones and amidines. The use of molecular iodine in a catalytic amount facilitates the functionalization of the sp3 C-H bond of acetophenones. This is a simple and efficient methodology for the synthesis of 1,3,5-triazines in good to excellent yields under transition-metal-free and peroxide-free conditions. The reaction is believed to take place via an in situ iodination-based oxidative elimination of formaldehyde. DFT calculations at the M062X/6-31+G(d,p) level were employed to investigate the reaction mechanism. Reaction barriers for the cycloaddition as well as a formaldehyde expulsion steps were computed, and a multistep mechanism starting with the nucleophilic attack by benzamidine on an in situ generated imine intermediate has been proposed. Both local and global reactivity descriptors were used to study the regioselectivity of the addition steps.
Tiwari, Abhishek R.,Nath, Shilpa R.,Joshi, Kaustubh A.,Bhanage, Bhalchandra M.
p. 13239 - 13249
(2017/12/26)

Oxalyl Boronates Enable Modular Synthesis of Bioactive Imidazoles
Described herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic, heteroaromatic, and alkyl carboxaldehydes were condensed with oxalyl boronates to afford substituted boryl imidazoles in a regiocontrolled fashion. Subsequent palladium-catalyzed cross-coupling with haloarenes furnished the desired trisubstituted imidazole scaffolds. To demonstrate the utility of these scaffolds, potent inhibitors of the serine/threonine-protein kinase STK10 were synthesized.
Lee, C. Frank,Holownia, Aleksandra,Bennett, James M.,Elkins, Jonathan M.,St. Denis, Jeffrey D.,Adachi, Shinya,Yudin, Andrei K.
p. 6264 - 6267
(2017/05/19)

Base-Mediated Syntheses of Di- and Trisubstituted Imidazoles from Amidine Hydrochlorides and Bromoacetylenes
A new transition metal-free method for the preparation of substituted imidazoles from easy-to-handle amidine hydrochlorides and bromoacetylenes has been developed. The reactions proceed in air and use inexpensive K2CO3 as base. Additions of 2,2′-bipyridine and water have beneficial effects on the product yields. Various di- and trisubstituted imidazoles have been prepared in good yields (up to 88%). A new transition metal-free method for the preparation of di- and trisubstituted imidazoles in good yields from easy-to-handle amidine hydrochlorides and bromoacetylenes has been developed. The reactions proceed in air and use inexpensive K2CO3 as base. Additions of 2,2′-bipyridine and water have beneficial effects on the product yields.
Chen, Xiao Yun,Englert, Ulli,Bolm, Carsten
supporting information
p. 13221 - 13224
(2015/09/15)

One-pot Synthesis of Polysubstituted Imidazoles Catalyzed by an Ionic liquid
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Maleki, Behrooz,Kahoo, Golnoosh Esmailian,Tayebee, Reza
p. 461 - 472
(2015/11/09)

Imidazoles from nitroallylic acetates and α-bromonitroalkenes with amidines: Synthesis and trypanocidal activity studies
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.
p. 9862 - 9871
(2015/10/05)

Synthesis of Imidazoles and Pyrimidines Using Palladium-Catalyzed Decarboxylative Intramolecular Condensation of 1,2,4-Oxadiazol-5(4 H)-ones
We found that 1,2,4-oxadiazol-5(4H)-ones acted as iminonitrene equivalents in the presence of a palladium catalyst and a stoichiometric amount of phosphine and that aza-Wittig-type condensation with the internal carbonyl moiety occurred to afford the corresponding imidazoles and pyrimidines. Georg Thieme Verlag Stuttgart. New York.
Shimbayashi, Takuya,Okamoto, Kazuhiro,Ohe, Kouichi
p. 1916 - 1920
(2014/08/18)

Suzuki-Miyaura cross-coupling reactions of unprotected haloimidazoles
An efficient protocol for the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of unprotected haloimidazoles is reported. The relatively mild reaction conditions allow for ready access to a wide array of functionalized imidazole derivatives in good to excellent yields. The synthetic utility of this method is demonstrated by the total synthesis of nortopsentin D.
Tan, Jiajing,Chen, Yonggang,Li, Hongmei,Yasuda, Nobuyoshi
p. 8871 - 8876
(2015/01/08)

Practical synthesis of polysubstituted imidazoles via iodine- Catalyzed aerobic oxidative cyclization of aryl ketones and benzylamines
A practical synthetic method for polysubstituted imidazoles via iodine-catalyzed aerobic oxidative cyclization of aryl ketones and benzylamines has been developed. It was found to tolerate a broad range of substrates to prepare polysubstituted imidazole derivatives in a one-pot manner, and thus importantly allowed product diversity for imidazole chemistry. Additionally, the resultant 1,2,4-trisubstituted imidazoles could be conveniently transformed to functionalized 1,2,4,5-tetrasubstituted imidazoles via electrophilic substitution or direct C-H functionalization, or 2,4-diaryl-1H-imidazoles by debenzylation reaction, which further indicates potential applications of this method in synthetic and pharmaceutical chemistry. Copyright
Huang, Huawen,Ji, Xiaochen,Wu, Wanqing,Jiang, Huanfeng
p. 170 - 180
(2013/03/13)

Catalytic electrophilic halogenation of silyl-protected and terminal alkynes: Trapping gold(I) acetylides vs. a Bronsted acid-promoted reaction
In the presence of a cationic gold(I) catalyst and N-halosuccinimide, both trimethylsilyl-protected and terminal alkynes are converted into alkynyl halides. Further experiments showed that silyl-protected alkynes undergo electrophilic iodination and bromination under Bronsted acid catalysis, whilst terminal alkynes require a cationic gold catalyst. The former reactions probably proceed via activation of the electrophile, whilst the latter reactions proceed via a gold(I) acetylide intermediate. Gold-catalysed halogenation was further combined with gold-catalysed hydration and subsequent annulation to provide convenient routes to iodomethyl ketones and five-membered aromatic heterocycles. Copyright
Starkov, Pavel,Rota, Filippo,D'Oyley, Jarryl M.,Sheppard, Tom D.
p. 3217 - 3224
(2013/01/15)

A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water
A simple, efficient and high yielding greener protocol for the synthesis of substituted thiazoles and imidazoles is described that utilizes the reaction of readily available α-tosyloxy ketones with variety of thioamides/amidines in water.
Kumar, Dalip,Kumar, N. Maruthi,Patel, Gautam,Gupta, Sudeep,Varma, Rajender S.
experimental part
p. 1983 - 1986
(2011/04/25)

Anticonvulsant activity of 2,4(1H)-diarylimidazoles in mice and rats acute seizure models
2,4(1H)-Diarylimidazoles have been previously shown to inhibit hNa V1.2 sodium (Na) channel currents. Since many of the clinically used anticonvulsants are known to inhibit Na channels as an important mechanism of their action, these compounds were tested in two acute rodent seizure models for anticonvulsant activity (MES and scMet) and for sedative and ataxic side effects. Compounds exhibiting antiepileptic activity were further tested to establish a dose response curve (ED50). The experimental data identified four compounds with anticonvulsant activity in the MES acute seizure rodent model (compound 10, ED50 = 61.7 mg/kg; compound 13, ED 50 = 46.8 mg/kg, compound 17, ED50 = 129.5 mg/kg and compound 20, ED50 = 136.7 mg/kg). Protective indexes (PI = TD 50/ED50) ranged from 2.1 (compound 10) to greater than 3.6 (compounds 13, 17 and 20). All four compounds were shown to inhibit hNa V1.2 in a dose dependant manner. Even if a correlation between sodium channel inhibition and anticonvulsant activity was unclear, these studies identify four Na channel antagonists with anticonvulsant activity, providing evidence that these derivatives could be potential drug candidates for development as safe, new and effective antiepileptic drugs (AEDs).
Zuliani, Valentina,Fantini, Marco,Nigam, Aradhya,Stables, James P.,Patel, Manoj K.,Rivara, Mirko
experimental part
p. 7957 - 7965
(2011/01/13)

2,4(5)-Diarylimidazoles: Synthesis and biological evaluation of a new class of sodium channel blockers against hNav1.2
A small family of novel 2,4(5)-diarylimidazoles were prepared through a simple and efficient synthesis and evaluated as potential inhibitors of hNav1.2 sodium channel currents. One member of this series (4) exhibited profound inhibition of Nav1.2 currents, emerging as a promising lead compound for further structure-activity relationship studies for the development of novel sodium channel blockers.
Rivara, Mirko,Baheti, Aparna R.,Fantini, Marco,Cocconcelli, Giuseppe,Ghiron, Chiara,Kalmar, Christopher L.,Singh, Natasha,Merrick, Ellen C.,Patel, Manoj K.,Zuliani, Valentina
experimental part
p. 5460 - 5462
(2009/05/26)

Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles
Stable and readily available 1-sulfonyl triazoles are converted to the corresponding imidazoles in good to excellent yields via a rhodium(II)-catalyzed reaction with nitriles. Rhodium iminocarbenoids are proposed intermediates. Copyright
Horneff, Tony,Chuprakov, Stepan,Chernyak, Natalia,Gevorgyan, Vladimir,Fokin, Valery V.
supporting information; experimental part
p. 14972 - 14974
(2009/03/12)

A practical synthesis of 2,4(5)-diarylimidazoles from simple building blocks
(Chemical Equation Presented) A simple and efficient approach to selectively obtain 2,4(5)-diarylimidazoles suppressing formation of 2-aroyl-4(5)-arylimidazoles is described. The yield of each of the two products strongly depends on the reaction condition
Zuliani, Valentina,Cocconcelli, Giuseppe,Fantini, Marco,Ghiron, Chiara,Rivara, Mirko
p. 4551 - 4553
(2008/02/05)

Preparation of 2,4-disubstituted imidazoles: 4-(4-Methoxyphenyl)-2-phenyl-1H-Imidazole [1H-Imidazole, 4-(4-methoxyphenyl)-2-phenyl-]
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Li, Bryan,Chiu, Charles K-F,Hank, Richard F.,Murry, Jerry,Roth, Joshua,Tobiassen, Harry,Kontnik, Renee,Wolff, Steven
p. 105 - 111
(2017/09/15)

Environmentally benign preparation of heteroaromatics from ketones or alcohols, with macroporous polystyrenesulfonic acid and (diacetoxyiodo)benzene, followed by thioamide, amidine, and 2-aminopyridine
An operationally simple, efficient, and environmentally benign preparation of heteroaromatics such as thiazoles, imidazoles, and imidazo[1,2-a]pyridines from the reactions of a polymer-supported [hydroxy(sulfonyloxy)iodo]benzene (2) with ketones or alcohols, followed by treatment with thioamides, benzamidine, and 2-aminopyridine, respectively, in the presence of potassium carbonate were successfully carried out.
Ueno, Makoto,Togo, Hideo
p. 2673 - 2677
(2007/10/03)

Novel oxidative α-tosyloxylation of alcohols with iodosylbenzene and p-toluenesulfonic acid and its synthetic use for direct preparation of heteroaromatics
α-Tosyloxyketones and α-tosyloxyaldehydes were directly prepared from alcohols by treatment with iodosyl-benzene and p-toluenesulfonic acid monohydrate in good yields. This method can be used for the direct preparation of thiazoles, imidazoles, and imidaz
Ueno, Makoto,Nabana, Takahiro,Togo, Hideo
p. 6424 - 6426
(2007/10/03)

Selective C-arylation of free (NH)-heteroarenes via catalytic C-H bond functionalization
A new system for palladium-catalyzed arylation of a broad spectrum of free (NH)-heteroarenes has been developed (indole, pyrrole, pyrazole, 2-phenylimidazole, imidazole, benzimidazole, and purine). Remarkable selectivity has been achieved in the presence of MgO base, providing single C-arylation products, while no N-arylation and no bis-arylation products have been detected. In the case of free imidazole, exclusive C-4 arylation may be switched to exclusive 2-arylation by the addition of CuI to the Pd/Ph3P/MgO system. When free aryl-(NH)-azoles are desired, direct arylation eliminates three steps in comparison to standard methods, including N-protection, stoichiometric metalation or halogenation, and N-deprotection. Copyright
Sezen, Bengue,Sames, Dalibor
p. 5274 - 5275
(2007/10/03)

Diversity synthesis via C-H bond functionalization: Concept-guided development of new C-arylation methods for imidazoles
Herein, we have formulated the concept of systematic derivatization of a structural motif via C-H bond functionalization. This concept may not only serve as a blueprint for new strategies in diversity synthesis but also provide systematic guidance for the
Sezen, Bengue,Sames, Dalibor
p. 10580 - 10585
(2007/10/03)

An optimized process for formation of 2,4-disubstituted imidazoles from condensation of amidines and α-haloketones
The preparation of 2,4-disubstituted imidazoles from the condensation of α-haloketones with amidines is described. The optimal reaction protocol is to add the α-bromoketone solution to the amidine in aqueous tetrahydrofuran in the presence of potassium bi
Li, Bryan,Chiu, Charles K.-F.,Hank, Richard F.,Murry, Jerry,Roth, Joshua,Tobiassen, Harry
p. 682 - 683
(2013/09/06)

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
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
p. 2075 - 2077
(2007/10/03)

Flash vacuum pyrolysis over solid catalysts. 1. Pyrazoles over zeolitest
Flash vacuum pyrolysis (fvp) reactions of 1H-pyrazole (1), 3,5-dimethylpyrazole (2), and 3,5-diphenylpyrazole (3) were carried out over zeolites. Reactions were performed using ZCOY-7, NH4-Y, and Na-Y zeolites. Reaction temperatures of heterogeneous reactions were lower than the corresponding temperatures in the homogeneous system, showing a catalytic effect of the zeolites. Compounds 1-3 afforded nitrogen extrusion in homogeneous fvp reactions while in the heterogeneous ones different reactions were present. Compounds 1 and 2 also afforded nitrogen extrusion; products arising from ring fragmentation were found in reactions of 2 and 3 while an isomeric imidazole was isolated in reactions of 3. Isomerization of 3 is attributed to a transition-state selectivity by the catalyst due to the relation between the size of the molecule and the cavity of the zeolite. This isomerization reaction was present only when zeolites with active Broensted sites were used.
Moyano,Yranzo
p. 2943 - 2947
(2007/10/03)

Thiadiazolium ylides: Substituted 2H-1,3,5-thiadiazines and 1,4,5-trisubstituted-imidazoles from 1,2,4- and 1,2,5-thiadiazolium-2-unsubstituted methanide (ylide) systems: Ring expansions and ring interconversions via sulfur-nitrogen heterotriene intermediates. Mechanistic ab initio calculations. Azolium 1,3-dipoles
Quaternisation of 3,5-diaryl-1,2,4-thiadiazoles with trimethylsilylmethyl triflate at 40°C occurred at N-2. Separate desilylation of the salts resulted in a ring expansion to substituted 2H-1,3,5-thiadiazines 5. Heating of these with ethanolic sodium ethoxide caused sulfur extrusion and ring contraction to 2,4-disubstituted imidazoles 6. 3,4-Diaryl-1,2,5-thiadiazoles were less reactive to alkylation and trimethylsilylmethylation required heating at 80°C. Treatment of the salts with CsF unexpectedly gave 1-trimethylsilylmethyl-4,5-diarylimidazoles 21.1H, 13C, 15N NMR spectra are described and the mechanisms were studied by ab inito calculations with the GAUSSIAN94 series of programmes using the HF/6-31G* theoretical level.
Butler, Richard N.,Cloonan, Martin O.,McMahon, John M.,Burke, Luke A.
p. 1709 - 1712
(2007/10/03)

Dehydrogenation of Imidazolines to Imidazoles with Pd-Carbon
A new and mild method for converting imidazoline derivatives to imidazole derivatives using Pd-C is described.The dehydrogenation of 2- and 2,4-disubstituted imidazolines is carried out in refluxing toluene using Pd-C in good yields.Mixed results are obtained with 4-substuted imidazolines.
Amemiya, Yoshiya,Miller, Duane D.,Hsu, Fu-Lian
p. 2483 - 2489
(2007/10/02)

Tricyclic Heteroaromatic Systems Containing a Bridgehead Nitrogen Atom. Part 2. Imidazoisothiazolopyrimidines and Pyrazolodipyrimidines.
Cyclisation of the N-phenacyl derivative (3) of 3-acetoacetylamido-4-methyl-6-phenylisothiazolopyrimidine gives an imidazoisothiazolopyrimidine (4) (36percent); an imidazobenzoisothiazole (7) is obtained analogously vi
Golec, Julian M. C.,Scrowston, Richard M.
p. 2580 - 2595
(2007/10/02)

Diphenylimidazole type dyes
A diphenylimidazole type cyan dye represented by the following Formula [I] or [II] is disclosed. The dye is capable of displaying relatively more preferable absorption characteristics so as to serve as a cyan dye, and suitable to be use in photographic, t
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(2008/06/13)

THERMOLYSIS OF 4-AZIDOPYRIMIDINES AND 4-AZIDOQUINAZOLINES
A facile thermolysis of 4-azidopyrimidines and 4-azidoquinazolines leading, by ring contraction, in excellent yields to 1-cyanoimidazoles and benzimidazoles is reported.
Giammanco, Lorenzo,Invidiata, Francesco Paolo
p. 1459 - 1464
(2007/10/02)

Synthesis of Imidazoles from Alkenes
Alkenes are converted into imidazoles through their epoxides by a sequence involving ring-opening with readily available 2-tributylstannyltetrazoles (8), dehydration of the resulting alcohols (9) using methyltriphenoxyphosphonium iodide in a improved procedure to give 1-alkenyltetrazoles (12), which give imidazoles (17) on photolysis.
Casey, Michael,Moody, Christopher J.,Rees, Charles W.
p. 1933 - 1941
(2007/10/02)

SYNTHESIS OF IMIDAZOLE DERIVATIVES FROM α-HALOOXIMES AND AMIDINES BY USE OF IRON CARBONYLS
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
p. 341 - 342
(2007/10/02)

Synthesis of Some Alkyl- and Arylimidazoles
The pyrolysis of 2-azidopyrazines led to give 1-cyanoimidazoles, which were hydrolyzed in alkaline and acidic media to the corresponding imidazoles.This ring transformation occured also by photolysis.
Watanabe, T.,Nishiyama, J.,Hirate, R.,Uehara, K.,Inoue, M.,et al.
p. 1277 - 1281
(2007/10/02)

A New Synthesis of Imidazoles
Alkenes are converted into imidazoles through their epoxides by treatment with 2-tri-n-butylstannyltetrazoles (2), followed by dehydration with methyltriphenoxyphosphonium iodide in an improved procedure, and photolysis of the resulting vinyltetrazoles (4).
Casey, Michael,Moody, Christopher J.,Rees, Charles W.
p. 714 - 715
(2007/10/02)

OXIDATION OF 2,4-DISUBSTITUTED PYRIMIDINES WITH ORGANIC PERACIDS
While 4,6-disubstituted (alkyl, aryl, alkoxyl) pyrimidines easily afforded the corresponding mono-N-oxides with hydrogen peroxide in glacial acetic acid, pyrimidine derivatives whose 6-position is free, are partly oxidatively degradated during N-oxidation reaction.The oxidation of the latter compounds under the above conditions gave 2,4-disubstituted imidazoles together with their mono-N-oxides.A likely mechanism of this ring-contraction and the improved conditions for the synthesis of the N-oxides are also described.
Yamanaka, Hiroshi,Ogawa, Shigeru,Sakamoto, Takao
p. 573 - 576
(2007/10/02)