Heterocyclizations via TosMIC-Based Multicomponent Reactions: A New Approach to One-Pot Facile Synthesis of Substituted Quinoxaline Derivatives

被引:27
作者
Neochoritis, Constantinos [1 ]
Idou-Stephanatou, Julia Stephan [1 ]
Tsoleridis, Constantinos A. [1 ]
机构
[1] Univ Thessaloniki, Organ Chem Lab, Dept Chem, Thessaloniki 54124, Macedonia, Greece
关键词
multicomponent reactions; TosMIC; quinoxalines; TYROSINE KINASE-ACTIVITY; ALPHA-HYDROXY KETONES; RECEPTOR ANTAGONISTS; O-PHENYLENEDIAMINES; OXIDATION PROCESSES; TANDEM OXIDATION; AMMONIUM-NITRATE; EFFICIENT; ANTIMYCOBACTERIAL; CYCLIZATION;
D O I
10.1055/s-0028-1087518
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel multicomponent reaction involving o-phenylenediamines, aldehydes and p-toluenesulfonylmethyl isocyanide (TosMIC) in the presence of a base leading to the formation of quinoxalines in very good yields is described.
引用
收藏
页码:302 / 305
页数:4
相关论文
共 54 条
  • [31] Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 1: SAR exploration and effective bioisosteric replacement of a phenyl substituent
    Myers, MR
    He, W
    Hanney, B
    Setzer, N
    Maguire, MP
    Zulli, A
    Bilder, G
    Galzcinski, H
    Amin, D
    Needle, S
    Spada, AP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (18) : 3091 - 3095
  • [32] Three-component tandem reactions of (2-arylsulfanyl-3-aryl-2-oxiranyl)(aryl)methanones and o-phenylenediamine:: formation of quinoxalines
    Nasar, M. Kamal
    Kumar, Raju Ranjith
    Perumal, Subbu
    [J]. TETRAHEDRON LETTERS, 2007, 48 (12) : 2155 - 2158
  • [33] Quinoxalinodehydroannulenes: A novel class of carbon-rich materials
    Ott, S
    Faust, R
    [J]. SYNLETT, 2004, (09) : 1509 - 1512
  • [34] Pearlman W.M., 1969, ORG SYN, V49, P75
  • [35] Piras Sandra, 2004, Farmaco (Lausanne), V59, P185, DOI 10.1016/j.farmac.2003.11.014
  • [36] MULTICOMPONENT ONE-POT ANNULATIONS FORMING 3 TO 6 BONDS
    POSNER, GH
    [J]. CHEMICAL REVIEWS, 1986, 86 (05) : 831 - 844
  • [37] Asymmetric multicomponent reactions (AMCRs):: The new frontier
    Ramón, DJ
    Yus, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) : 1602 - 1634
  • [38] Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds
    Raw, SA
    Wilfred, CD
    Taylor, RJK
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (05) : 788 - 796
  • [39] Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation
    Robinson, RS
    Taylor, RJK
    [J]. SYNLETT, 2005, (06) : 1003 - 1005
  • [40] SAKATA G, 1988, HETEROCYCLES, V27, P2481