HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids with arylaldehydes: one-pot synthesis of 1-arylisoquinolines

被引：4
|
作者：
Hsueh, Nai-Chen [1 ]
Chen, Shin-Mei [1 ]
Lin, Chun-Yi [1 ]
Chang, Meng-Yang [1 ,2 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
[2] Kaohsiung Med Univ Hosp, Dept Med Res, Kaohsiung 807, Taiwan
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 05期
关键词：
D O I：
10.1039/d0ob02431g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this paper, a concise, open-vessel synthesis of 1-arylisoquinolines is described via HCl-mediated intermolecular cyclocondensation of oxygenated arylacetic acids with arylaldehydes in the presence of NH2OH and alcoholic solvents under mild and one-pot reaction conditions. A plausible mechanism is proposed and discussed herein. In the overall reaction process, only water was generated as the byproduct. Various environmentally friendly reaction conditions are investigated for convenient transformation via the (4C + 1C + 1N) annulation. This protocol provides a highly effective ring closure via the formations of one carbon-carbon (C-C) bond, two carbon-nitrogen (C-N) bonds and one carbon-oxygen (C-O) bond.
引用
收藏
页码：1047 / 1059
页数：13
相关论文
共 50 条
  • [1] One-Pot Amberlyst 15-Controlled Cyclocondensation of Piperidines and Arylaldehydes: Synthesis of 3,5-Diarylmethylpyridines
    Chang, Meng-Yang
    Tsai, Yu-Lin
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08): : 5651 - 5659
  • [2] KI mediated one-pot cascade reaction for synthesis of 1,3,4-selenadiazoles
    Datta, Kumaresh
    Mitra, Bijeta
    Pariyar, Gyan Chandra
    Ghosh, Pranab
    RSC ADVANCES, 2024, 14 (22) : 15449 - 15454
  • [3] One-pot synthesis of sulfonyl dibenzosuberdiones via In(OTf)3-promoted double Friedel-Crafts reactions of oxygenated arylacetic acids with β-arylvinyl sulfones
    Chang, Meng-Yang
    Lin, Chun-Yi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (11) : 2405 - 2416
  • [4] Synthesis of Cytimidine through a One-Pot Copper-Mediated Amidation Cascade
    Serrano, Catherine M.
    Looper, Ryan E.
    ORGANIC LETTERS, 2011, 13 (19) : 5000 - 5003
  • [5] Tandem cyclocondensation of 1,3-bis-sulfonylpropan-2-ones with arylaldehydes. One-pot synthesis of tris-sulfonyl 3-arylphenols
    Hsueh, Nai-Chen
    Chang, Meng-Yang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (43) : 8471 - 8483
  • [6] Oxidative decarboxylation of arylacetic acids in water: One-pot transition-metal-free synthesis of aldehydes and ketones
    Mete, Trimbak B.
    Khopade, Tushar M.
    Bhat, Ramakrishna G.
    TETRAHEDRON LETTERS, 2017, 58 (29) : 2822 - 2825
  • [7] Se-mediated one-pot synthesis of 2-substituted benzoselenazole derivatives from 2 to iodoanilines and arylacetic acids/arylmethyl chlorides
    Gu, Ren
    Wang, Xin
    Yan, Zhao
    Han, Shiqing
    TETRAHEDRON LETTERS, 2018, 59 (29) : 2835 - 2838
  • [8] One-Pot Access to 4-Aryl-2-arylacetoxynaphthalenes via Benz-annulation of Oxygenated Arylacetic Acids and Alkyl Aryl Ketones
    Chang, Meng-Yang
    Chen, Shin-Mei
    Hsiao, Yu-Ting
    SYNTHESIS-STUTTGART, 2020, 52 (07): : 1035 - 1046
  • [9] One-pot synthesis of optically active tetramic acids from amino acids mediated by 1-hydroxybenzotriazole
    Athanasellis, G
    Gavrielatos, E
    Igglessi-Markopoulou, O
    SYNLETT, 2001, (10) : 1653 - 1655
  • [10] One-Pot Synthesis of Phenylglyoxylic Acid from Racemic Mandelic Acids via Cascade Biocatalysis
    Tang, Cun-Duo
    Ding, Peng-Ju
    Shi, Hong-Ling
    Jia, Yuan-yuan
    Zhou, Mao-zhi
    Yu, Hui-lei
    Xu, Jian-He
    Yao, Lun-Guang
    Kan, Yun-Chao
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2019, 67 (10) : 2946 - 2953
12345