Microwave-assisted Synthesis of 6-{(5-Aryl-1,3,4-oxadiazol-2-yl)methyl}-6H-indolo[2,3-b]quinoxalines

被引:4
作者
Avula, Sreenivas [1 ]
Komsani, Jayaram Reddy [1 ]
Koppireddi, Satish [1 ]
Yadla, Rambabu [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Fluoroorgan Div, Hyderabad 500607, Andhra Pradesh, India
关键词
ORGANIC-SYNTHESIS; DERIVATIVES; AGENTS; 1,3,4-OXADIAZOLES; QUINOXALINES; QUINOLINES; INHIBITORS; CHEMISTRY;
D O I
10.1002/jhet.2272
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and convenient synthesis of a new series of 2-{(6H-indolo[2,3-b]quinoxalin-6-yl)methyl}-5-aryl-1,3,4-oxadiazoles from readily available 1,2-diaminobenzene and isatins under microwave irradiation conditions was disclosed. The 6-{(5-aryl-1,3,4-oxadiazol-2-yl)methyl}-6H-indolo[2,3-b]quinoxalines were also prepared by the thermal cyclo-condensation reaction of 2-(6H-indolo[2,3-b]quinoxalin-6-yl)acetohydrazides with carboxylic acids in refluxing POCl3. The microwave-assisted synthesis was rapid and resulted in higher yield of the products at lower operating temperature with reduced waste generation in comparison with the thermal reaction protocol.
引用
收藏
页码:1737 / 1742
页数:6
相关论文
共 32 条
  • [1] Abadi AH, 1998, ARCH PHARM, V331, P352, DOI 10.1002/(SICI)1521-4184(199811)331:11<352::AID-ARDP352>3.0.CO
  • [2] 2-2
  • [3] 3,3-DIPHENYL-3-(2-ALKYL-1,3,4-OXADIAZOL-5-YL)PROPYLCYCLOALKYLAMINES, A NOVEL SERIES OF ANTIDIARRHEAL AGENTS
    ADELSTEIN, GW
    YEN, CH
    DAJANI, EZ
    BIANCHI, RG
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (10) : 1221 - 1225
  • [4] Angelini I., 1969, CHEM ABSTR, V71, Patent No. 1,161,801
  • [5] [Anonymous], 2000, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that grow Aerobically, V5th
  • [6] The chemistry of pseudomonic acid .18. Heterocyclic replacement of the alpha,beta-unsaturated ester: Synthesis, molecular modeling, and antibacterial activity
    Brown, P
    Best, DJ
    Broom, NJP
    Cassels, R
    OHanlon, PJ
    Mitchell, TJ
    Osborne, NF
    Wilson, JM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (16) : 2563 - 2570
  • [7] MICROWAVE-ASSISTED ORGANIC-REACTIONS
    CADDICK, S
    [J]. TETRAHEDRON, 1995, 51 (38) : 10403 - 10432
  • [8] Quinoxaline 1,4-dioxide: A versatile scaffold endowed with manifold activities
    Carta, A
    Corona, P
    Loriga, M
    [J]. CURRENT MEDICINAL CHEMISTRY, 2005, 12 (19) : 2259 - 2272
  • [9] Synthesis and antitumor properties of N-[2-(dimethylamino)ethyl]carboxamide derivatives of fused tetracyclic quinolines and quinoxalines: A new class of putative topoisomerase inhibitors
    Deady, LW
    Kaye, AJ
    Finlay, GJ
    Baguley, BC
    Denny, WA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (13) : 2040 - 2046
  • [10] Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities
    Dogan, HN
    Duran, A
    Rollas, S
    Sener, G
    Uysal, MK
    Gülen, D
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (09) : 2893 - 2898