3034-50-2Relevant articles and documents
Regioselective n-alkylation of 4-formylimidazole
Su, Qiaogong,Wood, Jeffery L.
, p. 3383 - 3389 (2000)
We describe here a high yield and highly regioselective N-alkylation of 4-formylimidazole via reversible Michael Reaction.
Urocanic acid photobiology. Purine-assisted photooxidation to 1H- imidazole-4(5)-carboxaldehyde
Mohammad,Kasper,Morrison
, p. 4903 - 4906 (1994)
Urocanic acid undergoes photooxidative cleavage at the acrylic acid side chain to afford imidazole carboxaldehyde. The reaction is accelerated in the presence of purines. Evidence is presented that the photooxidation involves a reaction of the UA radical cation and ground state molecular oxygen.
A simple and efficient synthesis of N-protected imidazole-4-carbaldehyde
Winter,Retey
, p. 245 - 246 (1994)
Successive addition of BuLi, triethylsilyl chloride, s-BuLi and DMF to 1- (N,N-dimethylsulfamoyl)imidazole (1) yields pure 1-(N,N-dimethylsulfamoyl)- 2-(triethylsilyl)imidazole-4-carbaldehyde (2) as judged by 1H NMR spectroscopy. Treatment of 2 with 2 N HCl leads to free imidazole-4- carbaldehyde (3) (overall yield 70.2%).
Method for preparing 1H-imidazole-4-carbonitrile
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Paragraph 0034; 0043-0049, (2019/02/26)
The invention discloses a method for preparing 1H-imidazole-4-carbonitrile, and particularly relates to the technical field of fine chemical product preparation. The method for preparing 1H-imidazole-4-carbonitrile comprises the following steps: step (1) oxidation reaction: performing oxidation on 4-hydroxymethylimidazole to obtain 1H-imidazole-4-carboxaldehyde; step (2) oximation reaction: performing oximation reaction on the 1H-imidazole-4-carboxaldehyde prepared in the step (1) to obtain 4-formaldoximido imidazole; and step (3) dehydration reaction: performing dehydration reaction on the 4-formaldoximido imidazole prepared in the step (2) to obtain 1H-imidazole-4-carbonitrile. The method provided by the invention has the advantages of reducing many steps due to intermediates are not purified from the beginning of the reaction to the end of the process, reducing energy consumption due to high and low temperature equipment is not used, reducing environmental pollution due to acidic wastewater is not generated, and having a high yield of products; the invention proposes a complete process route for synthesizing 1H-imidazole-4-carbonitrile by using 4-hydroxymethylimidazole as a rawmaterial; and the method is simple in process and easy to realize industrial production.
Synthesis method of 1H-imidazole-4-carboxylic acid
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Paragraph 0021; 0028; 0035; 0042; 0049, (2018/05/16)
The invention discloses a synthesis method of 1H-imidazole-4-carboxylic acid. The method comprises steps as follows: (1) a hydrochloric acid solution is added to a reaction kettle, chromium trioxide is added under the stirring condition, the mixture is stirred uniformly and heated to 40-50 DEG C, pyridine is dropwise added, the mixture is stirred to react for 2-3 h after pyridine is dropwise added, PCC (pyridinium chlorochromate) is prepared, TiO2 is added, a dichloromethane solution of 4-methylimidazole is dropwise added under the stirring condition, the mixture is subjected to a reaction at40-50 DEG C for 3-4 h, then, filtration and centrifugation are performed, an organic layer is collected, reduced pressure distillation is performed, and 1H-imidazole-4-formaldehyde is prepared; (2) prepared 1H-imidazole-4-formaldehyde and dichloromethane are mixed, the obtained mixture is heated to 40-50 DEG C, KMnO4 is added, the mixture is mixed uniformly and stirred for a reaction for 3-4 h, filtration, reduced pressure distillation and recrystallization are performed, and 1H-imidazole-4-carboxylic acid is prepared. The synthesis method is simple to operate and mild in condition, fewer by-products are produced, the product purity is high and the product yield is higher.
Hydrazinyl-Substituted Heteroaryl Compounds and Methods for Producing a Conjugate
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Paragraph 0540-0542, (2017/09/29)
The present disclosure provides conjugate structures and hydrazinyl-substituted heteroaryl compounds used to produce these conjugates. The disclosure also encompasses methods of production of such conjugates and compounds, as well as methods of using the same.
Halogen–metal exchange on bromoheterocyclics with substituents containing an acidic proton via formation of a magnesium intermediate
Tian, Qingqiang,Shang, Suqin,Wang, Huajun,Shi, Guoqiang,Li, Zhiyao,Yuan, Jianyong
supporting information, (2017/12/05)
A selective and practical bromine–metal exchange on bromoheterocyclics bearing substituents with an acidic proton under non-cryogenic conditions was developed by a simple modification of an existing protocol. Our protocol of using a combination of i-PrMgCl and n-BuLi has not only solved the problem of intermolecular quenching that often occurred when using alkyl lithium alone as the reagent for halogen–lithium exchange, but also offered a highly selective method for performing bromo–metal exchange on dibrominated arene compounds through chelation effect.
An expedient osmium(vi)/K3Fe(CN)6-mediated selective oxidation of benzylic, allylic and propargylic alcohols
Fernandes, Rodney A.,Bethi, Venkati
, p. 40561 - 40568 (2015/02/18)
A chemoselective osmium(vi) catalyzed oxidation of benzylic, allylic and propargylic alcohols using K3Fe(CN)6as a secondary oxidant is described. This protocol is operationally simple and exhibits excellent chemoselectivity favouring the oxidation of benzylic alcohols over the aliphatic alcohols. A larger scale reaction was also found to be compatible. This journal is
PRODUCTION METHOD OF IMIDAZOLE DERIVATIVES
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Page/Page column 34-35, (2013/02/28)
The present invention provides an advantageous production method of an imidazole derivative, which is suitable for industrial production. Compound (VI) is produced by reacting compound (I) with a Grignard reagent or a magnesium reagent, and a lithium reagent, and then reacting the resulting compound with compound (V).
Design and synthesis of new 1,4-dihydropyridines containing 4(5)-chloro-5(4)-imidazolyl substituent as a novel calcium channel blocker
Iman, Maryam,Davood, Asghar,Nematollahi, Ali Reza,Dehpoor, Ahmad Rerza,Shafiee, Abbas
scheme or table, p. 1417 - 1426 (2012/05/04)
New analogues of nifedipine, in which the ortho-nitro phenyl group at position 4 has been replaced by 4(5)-chloro-5(4)-imidazolyl substituent and which are able to interact with the receptor by hydrogen binding were designed, synthesized, and evaluated as calcium channel antagonists. The designed dihydropyridines were synthesized using the Hantzsch condensation and evaluated as calcium channel antagonists using the high K+ contraction of guineapig ileal longitudinal smooth muscle. A docking study was performed using the AutoDock4 program, and QSAR equations were obtained using multilinear regression. Our computational studies indicated that the oxygen of the ester (O10) and the N3′ of the imidazole ring form a hydrogen bonding interaction with the NH of HIS 363 and NH of LYS354, respectively, and that the sum of the BEHp5 and RDF075p are the most significant descriptors. The results of calcium channel antagonist evaluation demonstrated that increasing the chain length in C3 and C5 ester substituents increased activity. The most potent compound was the bis-phenylpropyl ester (5l) derivative, in that it was more active than the reference drug nifedipine and that the bis-phenylethyl ester (5k) derivative had comparable activity with nifedipine. The present research revealed that the 4(5)-chloro-5(4)-imidazolyl moiety is a bioisoster of o-nitrophenyl in nifedipine and provided novel dihydropyridines with more activity as calcium channel antagonists.
