Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

被引：34
|
作者：
Ayaz, Muhammad
Xu, Zhigang
Hulme, Christopher [1 ]
机构：
[1] Univ Arizona, Oro Valley BIO5, Coll Pharm, Oro Valley, AZ 85737 USA
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 23期
关键词：
Ugi reaction; Post-condensation modifications; Quinoxaline; Benzimidazole; Acyl transfer; SOLUTION-PHASE PREPARATION; ONE-POT; DERIVATIVES; EFFICIENT; LIBRARIES; PROTOCOL; MILD;
D O I：
10.1016/j.tetlet.2014.04.013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a 'convertible carboxylic acid', which in addition may be captured in an intramolecular sense to generate structurally complex 2-benzimidazolylquinoxalines in a mere two steps. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3406 / 3409
页数：4
相关论文
共 50 条
  • [21] 5-Methyl-1,2,3-thiadiazoles Synthesized via Ugi Reaction and Their Fungicidal and Antiviral Activities
    Zheng, Qingxiang
    Mi, Na
    Fan, Zhijin
    Zu, Xiang
    Zhang, Haike
    Wang, Huan
    Yang, Zhikun
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (13) : 7846 - 7855
  • [22] Synthesis of 4-Methyl-1,2,3-thiadiazole Derivatives via Ugi Reaction and Their Biological Activities
    Zuo, Xiang
    Mi, Na
    Fan, Zhijin
    Zheng, Qingxiang
    Zhang, Haike
    Wang, Huan
    Yang, Zhikun
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (05) : 2755 - 2762
  • [23] Synthesis of novel norsufentanil analogs via a four-component Ugi reaction and in vivo, docking, and QSAR studies of their analgesic activity
    Nami, Majid
    Salehi, Peyman
    Dabiri, Minoo
    Bararjanian, Morteza
    Gharaghani, Sajjad
    Khoramjouy, Mona
    Al-Harrasi, Ahmed
    Faizi, Mehrdad
    CHEMICAL BIOLOGY & DRUG DESIGN, 2018, 91 (04) : 902 - 914
  • [24] Synthesis of indoline-piperidinones via a novel Ugi, ring expansion, pseudo-Dieckmann condensation and rearrangement cascade reaction
    Lei, Jie
    Song, Gui-Ting
    Luo, Ya-Fei
    Tang, Dian-Yong
    Yan, Wei
    Li, Hong-yu
    Chen, Zhong-Zhu
    Xu, Zhi-Gang
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (05) : 737 - 741
  • [25] Synthesis of novel glycopeptidomimetics via Nβ-protected-amino alkyl isonitrile based Ugi 4C reaction
    Vasantha, Basavalingappa
    Prabhu, Girish
    Basavaprabhu, Hosmani
    Sureshbabu, Vommina V.
    TETRAHEDRON LETTERS, 2013, 54 (33) : 4409 - 4413
  • [26] Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction
    Chen, Na
    Long, Tianyu
    Kong, Han-Han
    Wu, Zheng-Wei
    Yang, Qing-Qing
    Huang, Nianyu
    Wang, Long
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (10) : 2780 - 2785
  • [27] Synthesis of small and medium sized 2,2-disubstituted lactams via the ''intramolecular'' three component Ugi reaction
    Harriman, GCB
    TETRAHEDRON LETTERS, 1997, 38 (32) : 5591 - 5594
  • [28] Functionalization of Poplar cotton via azido-Ugi reaction: as a green biocatalytic system for the chemical fixation of CO2
    Nazeri, Mohammad Taghi
    Ghasemi, Maryam
    Torabi, Saeed
    Shaabani, Ahmad
    CELLULOSE, 2024, 31 (08) : 4929 - 4946
  • [29] Rh(III)-Catalyzed C-2 Alkylation of Indoles followed by a Post-Synthetic Modification via the Ugi Reaction
    Januario, Marcelo Augusto Pereira
    de Souza, Demetrius P.
    Zukerman-Schpector, Julio
    Correa, Arlene G.
    CHEMISTRYOPEN, 2023, 12 (06)
  • [30] A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent Ugi reaction
    Basso, A
    Banfi, L
    Riva, R
    Guanti, G
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02): : 575 - 579
12345