One-pot synthesis of quinoline-fused [1,4]thiazepines via the tandem Ugi/post-Ugi reactions

被引:3
|
作者
Ghandi, Mehdi [1 ]
Efteghar, Irene [1 ]
Abbasi, Alireza [1 ]
机构
[1] Univ Tehran, Sch Chem, Coll Sci, POB 14155 6455, Tehran, Iran
关键词
Pyrrolidine-2-ones; Ugi reaction; Piperazines; DIVERSITY-ORIENTED SYNTHESIS; COMBINATORIAL SYNTHESIS; DISCOVERY; LEAKY;
D O I
10.1007/s13738-018-1511-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A one-pot strategy has been developed for the synthesis of novel tetrahydro-[1,4]thiazepino[7,6-b]quinoline-5-carboxamide derivatives. These reactions presumably proceed by the combination of a Ugi 4CR and three intramolecular S(N)2 aliphatic, an alkaline hydrolysis and an intramolecular cyclization SNAr nucleophilic substitution processes in moderate to good yields. Unambiguous assignment of the molecular structures was carried out by single-crystal X-ray diffraction.
引用
收藏
页码:325 / 332
页数:8
相关论文
共 50 条
  • [1] One-pot synthesis of quinoline-fused [1,4]thiazepines via the tandem Ugi/post-Ugi reactions
    Mehdi Ghandi
    Irene Efteghar
    Alireza Abbasi
    Journal of the Iranian Chemical Society, 2019, 16 : 325 - 332
  • [2] One-Pot, Base- and Metal-Free Practical Synthesis of Novel Cycloalkene-Fused [1,4]Thiazepines through the Sequential Ugi/SNCsp2 Reactions
    Takallou, Ahmad
    Al-Shidhani, Sulaiman
    Anwar, Muhammad U.
    Al-Harrasi, Ahmed
    SYNTHESIS-STUTTGART, 2023, 55 (03): : 489 - 498
  • [3] Synthesis of Structurally Diverse Substituted Aziridinyl Glycoconjugates via Base-Mediated One-Pot Post-Ugi Cyclization
    Sangwan, Rekha
    Dubey, Atul
    Prajapati, Gurudayal
    Arripapathi, Ravi Sankar
    Mandal, Pintu Kumar
    ORGANIC LETTERS, 2019, 21 (08) : 2859 - 2862
  • [4] One-pot synthesis of spiropyrrolidine-pyrrolo[2,3-b]quinoline derivatives via metal-free post-Ugi bis-annulation reactions
    Fallahnezhad, Maryam
    Ghandi, Mehdi
    Abbasi, Alireza
    CHEMISTRYSELECT, 2023, 8 (26):
  • [5] Asymmetric Synthesis of Azepinoindoles via Enantioselective Ugi-4CR/post-Ugi Transformation Sequence
    Fang, Li-Ping
    Yu, Xin-Ran
    Han, Jia-Jun
    Jiang, Hua-Jie
    Yu, Jie
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [6] A new one-pot synthesis of pseudopeptide connected to sulfonamide via the tandem N-sulfonylation/Ugi reactions
    Nazeri, Mohammad Taghi
    Nowee, Ali Beygzade
    Shaabani, Ahmad
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (07) : 3479 - 3484
  • [7] Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction
    Li, Yong
    Huang, Zheng
    Xu, Jia
    Ding, Yong
    Tang, Ding-Yong
    Lei, Jie
    Li, Hong-yu
    Chen, Zhong-Zhu
    Xu, Zhi-Gang
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 663 - 669
  • [8] One-pot regioselective synthesis of β-lactams by a tandem Ugi 4CC/SN cyclization
    Zeng, Xiao-Hua
    Wang, Hong-Mei
    Yan, Yan-Mei
    Wu, Lei
    Ding, Ming-Wu
    TETRAHEDRON, 2014, 70 (23) : 3647 - 3652
  • [9] KOtBu-catalyzed protocol for the post-ugi synthesis of spiro-y-lactam-pyrrolo[2,3-b]quinoline derivatives in one-pot
    Fallahnezhad, Maryam
    Ghandi, Mehdi
    Rahimi, Shahnaz
    Abbasi, Alireza
    TETRAHEDRON, 2023, 140
  • [10] The Application of Multicomponent Ugi and Passerini Reactions for the One-Pot Synthesis of Pyrrolones and Butenolides
    Nechaev, Anton A.
    Peshkov, Anatoly A.
    Peshkov, Vsevolod A.
    Van der Eycken, Erik V.
    SYNTHESIS-STUTTGART, 2016, 48 (14): : 2280 - 2286