37009-52-2Relevant academic research and scientific papers
2, 5-substituent-1H-imidazole-4-carboxylic ester compound and synthesis and purification method thereof
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Paragraph 0103-0107, (2021/05/08)
The invention provides a 2, 5-substituent-1H-imidazole-4-carboxylic ester compound and a synthesis and purification method thereof, the method uses iodine as an oxidizing agent to promote the oxidative cyclization reaction of an enamine compound, so that the operation of preparing the 2, 5-substituent-1H-imidazole-4-carboxylic ester compound is simpler, the preparation cost is greatly reduced, the relative yield and purity are higher, and the environmental pollution is less. Besides, the 2, 5-substituent-1H-imidazole-4-carboxylic ester compound provided by the invention has been widely applied in the fields of medicine, ligand chemistry and material science due to the special heterocyclic skeleton, and is a valuable synthetic intermediate and a functional organic molecule.
Iodine-Mediated Cyclization of Enamines to Imidazole-4-Carboxylic Derivatives with Sequential Removal of Nitrogen Atoms from TMSN3
Bai, Zi-Jing,Chen, Huaijuan,Gao, Peng,Li, Yingchun,Wang, Xiaomei,Yang, Desuo,Zhang, Jiangwei,Zhang, Sheng,Zhao, Mi-Na
, p. 10492 - 10500 (2021/08/16)
An iodine-mediated oxidative [4+1] cyclization of enamines with TMSN3 for the synthesis of 2,5-disubstituted imidazole-4-carboxylic derivatives has been developed. The mechanistic studies revealed that the reaction proceeds through a sequential removal of two nitrogen atoms from TMSN3. The synthetic utility was further demonstrated with a gram-scale reaction and various derivatization transformations of the products.
Synthesis of polyfunctional imidazoles from vinyl azides and amidine along with NHBoc as a leaving group
Tang, Pai,Ke, Di,Shao,Chen, Wenteng,Yu, Yongping
, p. 4419 - 4424 (2019/07/09)
An efficient method for the synthesis of polyfunctional imidazoles from vinyl azides and amidine has been developed. Starting from vinyl azide and amidine, this transformation proceeds without any additives and the obtained imidazoles can be decorated with ester functional group that is a promising site for further modification.
ZnCl2-Catalyzed [3 + 2] Cycloaddition of Benzimidates and 2 H-Azirines for the Synthesis of Imidazoles
Shi, Shoujie,Xu, Kang,Jiang, Cheng,Ding, Zhenhua
, p. 14791 - 14796 (2018/11/23)
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.
A Domino Azidation/C-H Amination Approach toward Trifluoromethyl Substituted Imidazoles
Ma, Haichao,Zhang, Xiaoyan,Chen, Liangliang,Yu, Wei
, p. 11841 - 11847 (2017/11/24)
N-Alkyl enamines can be transformed into 2,4,5-trisubsituted imidazoles by reacting with (diacetoxyiodo)benzene and TMSN3 under the catalysis of a copper salt such as Cu(OAc)2. Tetrabutyl ammonium iodide was also capable of promoting the reaction. The transformation from N-alkyl enamines into 2,4,5-trisubsituted imidazoles took place in a domino azidation/intramolecular C(sp3)-H amination pattern. The present reaction provides a new efficient method for the preparation of 4-(trifluoromethyl) imidazoles.
A multi-substituted imidazole derivatives method for the preparation of
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, (2017/04/11)
The invention provides a preparation method of multifunctional group-substituted imidazole derivatives including derivatives of 2,4,5-trisubstituted imidazole and 2-amino-4,5-disubstituted imidazole, and the derivatives are generated by alkenyl nitrine de
Synthesis of poly-functionalized imidazoles via vinyl azides annulation
Luo, Jing,Chen, Wenteng,Shao, Jiaan,Liu, Xingyu,Shu, Ke,Tang, Pai,Yu, Yongping
, p. 55808 - 55811 (2015/07/20)
An efficient annulation of vinyl azides with activated imines has been developed for the synthesis of poly-functionalized imidazole derivatives. This reaction includes thermal decomposition of vinyl azides to 2H-azirines, nucleophilic attack of 2H-azirines with activated imines and subsequent cyclization to desired imidazoles.
Convenient synthesis of highly substituted imidazole derivatives
Wong, Lai Chun,Gehre, Alexander,Stanforth, Stephen P.,Tarbit, Brian
, p. 80 - 84 (2012/10/29)
A one-pot synthesis of the trisubstituted imidazole derivatives from α-acetoxy-α-chloro-β-keto-esters, aldehydes, and ammonium acetate has been developed. Copyright Taylor & Francis Group, LLC.
Synthesis of di- and tri-substituted imidazole-4-carboxylates via PBu3-mediated [3+2] cycloaddition
Hsu, Mei-Yuan,Dietrich, Justin,Hulme, Christopher,Shaw, Arthur Y.
, p. 1538 - 1542 (2013/05/21)
Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole- 4-carboxylates stemmed from the PBu3-mediated [3+2] cycloaddition between in situ-generated Δ2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7-20 were afforded in better yields than those of disubstituted imidazoles 21-27. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
Neurokinin-3 receptor modulators: diaryl imidazole derivatives
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Page/Page column 17, (2010/02/12)
The invention relates to compounds of general Formula I: wherein the variables are as defined herein. Also provided are pharmaceutical compositions comprising such compounds, and methods for treating patients suffering from a disorder responsive to neurok
