Highly Efficient Synthesis of Imidazolecarboxylate Salts via Sequential Nucleophilic Addition-Intramolecular Cyclization Reactions

被引:0
|
作者
Nazarahari, Maryam [1 ]
Azizian, Javad [1 ]
机构
[1] Islamic Azad Univ, Dept Chem, Sci & Res Branch, Tehran, Iran
关键词
Imidazole; amino acid; intramolecular cyclization; GAP chemistry; eprosartan; etomidate; PURIFICATION GAP CHEMISTRY; ONE-POT SYNTHESIS; IMIDAZOLES; ACID; DERIVATIVES; CATALYST; GREEN; CYCLOADDITION; IMINES; LIGAND;
D O I
10.2174/1570178619666220819152744
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this work, we used a highly efficient and easy approach for synthesizing imidazolecarboxylate salt through the reaction between alpha-amidino carboxylic acids and alpha-halo ketones with as readily available starting materials in the presence of KHCO3 at THF under reflux. Targeted synthesis of this type of imidazole bearing the carboxylic acid group in a single structure, in addition to the biological properties enriched as a ligand, is very popular in the manufacture of catalysts. The salient features of this protocol include eco-friendly, high atom-economical, easy and mild conditions that led to the production of all products with high yields. Furthermore, all products were purified without the need for column chromatography through the GAP chemistry (group-assisted purification chemistry) technique.
引用
收藏
页码:54 / 60
页数:7
相关论文
共 50 条
  • [1] Highly Efficient Chemoselective Synthesis of Pyrrolo[2,3-c]pyrazole Bearing Oxindole via Sequential Condensation-Michael Addition-Intramolecular Cyclization Reactions
    Nazeri, Mohammad Taghi
    Farhid, Hassan
    Javanbakht, Siamak
    Shaabani, Ahmad
    Notash, Behrouz
    SYNLETT, 2020, 31 (10) : 965 - 971
  • [2] Highly efficient synthesis of 2,3,4-trisubstituted furans via silver-catalyzed sequential nucleophilic addition and cyclization reactions of haloalkynes
    Zeng, Wei
    Wu, Wanqing
    Jiang, Huanfeng
    Sun, Yadong
    Chen, Zhengwang
    TETRAHEDRON LETTERS, 2013, 54 (35) : 4605 - 4609
  • [3] A facile and efficient carbodiimide-mediated synthesis of dihydroquinazolines via a tandem nucleophilic addition-intramolecular hetero conjugate addition annulation strategy
    Saito, T
    Tsuda, K
    Saito, Y
    TETRAHEDRON LETTERS, 1996, 37 (02) : 209 - 212
  • [4] Enantioselective synthesis of 5-LO inhibitor hydroxyureas. Tandem nucleophilic addition-intramolecular cyclization of chiral nitrones
    Lantos, I
    Flisak, J
    Liu, L
    Matsuoka, R
    Mendelson, W
    Stevenson, D
    Tubman, K
    Tucker, K
    Zhang, WY
    Adams, J
    Sorenson, M
    Garigipati, R
    Erhardt, K
    Ross, S
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16): : 5385 - 5391
  • [5] Diastereoselective enzymatic synthesis of highly substituted 3,4-dihydropyridin-2-ones via domino Knoevenagel condensation-Michael addition-intramolecular cyclization
    Liu, Zhi-Qiang
    Liu, Bo-Kai
    Wu, Qi
    Lin, Xian-Fu
    TETRAHEDRON, 2011, 67 (50) : 9736 - 9740
  • [6] Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions
    Cichowicz, Nathan R.
    Kaplan, Will
    Khomutnyk, Yaroslav
    Bhattarai, Bijay
    Sun, Zhankui
    Nagorny, Pavel
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (45) : 14341 - 14348
  • [7] Asymmetric Synthesis of (+)-Vellosimine Enabled by a Sequential Nucleophilic Addition/Cyclization Process
    Zou, Huanhuan
    Yan, Jiahang
    Zhang, Xiaocheng
    Wu, Xiaohui
    Huo, Jiyou
    Xu, Yuanzhen
    Xie, Weiqing
    ORGANIC LETTERS, 2023, 25 (46) : 8215 - 8219
  • [8] Tandem Nucleophilic Addition-Intramolecular Aza-Michael Reaction: Facile Synthesis of Chiral Fluorinated Isoindolines
    Fustero, Santos
    Moscardo, Javier
    Sanchez-Rosello, Maria
    Rodriguez, Elsa
    Barrio, Pablo
    ORGANIC LETTERS, 2010, 12 (23) : 5494 - 5497
  • [9] Efficient enantioselective synthesis of sertraline, a potent antidepressant, via a novel intramolecular nucleophilic addition to imine
    Chen, CY
    Reamer, RA
    ORGANIC LETTERS, 1999, 1 (02) : 293 - 294
  • [10] Synthesis of 2,4-methanoproline analogues via an addition-intramolecular substitution sequence
    Rammeloo, T
    Stevens, CV
    De Kimpe, N
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18): : 6509 - 6513