An Efficient Ultrasound-Assisted Synthesis of N-Alkyl Derivatives of Carbazole, Indole, and Phenothiazine

被引:18
作者
Zhao, Sanhu [1 ]
Kang, Jin [1 ]
Du, Yuting [1 ]
Kang, Jingyan [1 ]
Zhao, Xiaoni [1 ]
Xu, Yinfeng [1 ]
Chen, Ruixi [1 ]
Wang, Qianqian [1 ]
Shi, Xitao [1 ]
机构
[1] Xinzhou Teachers Univ, Dept Chem, Xinzhou 034000, Peoples R China
关键词
IONIC LIQUIDS; NITROGEN-HETEROCYCLES; PYRROLE; BENZOTRIAZOLE; CHEMISTRY; BASE;
D O I
10.1002/jhet.1652
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N-DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.
引用
收藏
页码:683 / 689
页数:7
相关论文
共 30 条
  • [1] Bo ZS, 1998, MACROMOL CHEM PHYSIC, V199, P1323, DOI 10.1002/(SICI)1521-3935(19980701)199:7<1323::AID-MACP1323>3.0.CO
  • [2] 2-J
  • [3] Ultrasound in heterocycles chemistry
    Cella, Rodrigo
    Stefani, Helio A.
    [J]. TETRAHEDRON, 2009, 65 (13) : 2619 - 2641
  • [4] N-alkylation of anilines, carboxamides and several nitrogen heterocycles using CsF-celite/alkyl halides/CH3CN combination
    Hayat, S
    Atta-ur-Rahman
    Choudhary, MI
    Khan, KM
    Schumann, W
    Bayer, E
    [J]. TETRAHEDRON, 2001, 57 (50) : 9951 - 9957
  • [5] Synthesis and optical properties of poly{(4-nitrophenyl)-[3-[N-[2-(methacryloyloxy)ethyl]-carbazolyol]]diazene}
    Ho, MS
    Barrett, C
    Paterson, J
    Esteghamatian, M
    Natansohn, A
    Rochon, P
    [J]. MACROMOLECULES, 1996, 29 (13) : 4613 - 4618
  • [6] New ionic liquids containing an appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide
    Holbrey, JD
    Turner, MB
    Reichert, WM
    Rogers, RD
    [J]. GREEN CHEMISTRY, 2003, 5 (06) : 731 - 736
  • [7] Ilmanr H., 1952, J AM CHEM SOC, V74, P4205
  • [8] Potassium carbonate as a base for the N-alkylation of indole and pyrrole in ionic liquids
    Jorapur, YR
    Jeong, JM
    Chi, DY
    [J]. TETRAHEDRON LETTERS, 2006, 47 (14) : 2435 - 2438
  • [9] Kang Y. S., 1991, J PHYS CHEM-US, V95, P1944
  • [10] KIKUGAWA Y, 1981, SYNTHESIS-STUTTGART, P461