SYNTHESIS AND FUNCTIONALIZATION OF THE 3-(1,3,4-OXADIAZOL-2-YL)-1H-INDOLES

被引:1
|
作者
Alyab'ev, S. B. [1 ]
Kravchenko, D. V. [1 ]
Ivashchenko, A. V. [1 ]
机构
[1] Res Inst Chem Divers, Chimki 141401, Moscow Region, Russia
关键词
3-(1,3,4-oxadiazol-2-yl)-1H-indoles; 3-(1,3,4-oxadiazol-2-yl)-1H-indol-1-yl]acetic acids; orthoesters; amide library; intramolecular cyclization; ANTIMICROBIAL ACTIVITY; DERIVATIVES; ANTAGONISTS; INDOLE;
D O I
10.1007/s10593-010-0418-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A modified method is proposed for the preparative synthesis of 3-(1,3,4-oxadiazol-2-yl)-1H-indoles in high yield. We are the first to demonstrate the functionalization of this heterocyclic system by alkylation. In particular, syntheses are reported for [3-(1,3,4-oxadiazol-2-yl)-1H-indol-1-yl]acetic acids and their amide derivatives.
引用
收藏
页码:1270 / 1275
页数:6
相关论文
共 50 条
  • [11] Synthesis of 3-(5-Aryl-1,3,4-oxadiazol-2-yl)chromones
    L. Tsao
    V. Van
    G. Sun
    Yu. Lyu
    Russian Journal of General Chemistry, 2001, 71 : 767 - 769
  • [12] The synthesis of 3-(5-aryl-1,3,4-oxadiazol-2-yl) chromones
    Cao, L
    Wang, W
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2003, (08): : 1227 - 1230
  • [13] 1-(1H-Benzimidazol-2-yl)-3-[5-( trichloromethyl)-1,3,4-oxadiazol-2-yl]propan-1-one
    Rashid, Mohd
    Husain, Asif
    Mishra, Ravinesh
    Ahmed, Niyaz
    Siddique, Nadeem Ahmed
    MOLBANK, 2012, (03)
  • [14] SYNTHESIS AND REACTIONS OF 3-(1,3,4-OXADIAZOL-2-YL)METHYLENE-2-OXO-1,2,3,4-TETRAHYDROQUINOXALINES
    KURASAWA, Y
    MORITAKI, Y
    EBUKURO, T
    TAKADA, A
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1983, 31 (11) : 3897 - 3901
  • [15] Synthesis and biological evaluation of 3-(azolylmethyl)-1H-indoles and 3-(α-azolylbenzyl)-1H-indoles as selective aromatase inhibitors
    Le Borgne, Marc
    Marchand, Pascal
    Nourrisson, Marie-Renee
    Loquet, Denis
    Palzer, Martina
    Le Baut, Guillaume
    Hartmann, Rolf W.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2007, 22 (05) : 667 - 676
  • [16] Synthesis and biological evaluation of 3-(1,3,4-oxadiazol-2-yl)-1,8-naphthyridin-4(1H)-ones as cisplatin sensitizers
    Hou, Xueyan
    Luo, Hao
    Zhang, Mengqi
    Yan, Guoyi
    Pu, Chunlan
    Lan, Suke
    Li, Rui
    MEDCHEMCOMM, 2018, 9 (11) : 1949 - 1960
  • [17] SYNTHESIS OF BIS(1,3,4-OXADIAZOL-2-YL)-5-ARYL-HYDRAZONES
    JANI, MK
    UNDAVIA, NK
    TRIVEDI, PB
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1989, 66 (04) : 281 - 282
  • [18] Efficient synthesis of 3-(4,5-dihydro-1H-imidazole-2-yl)-1H-indoles
    Hary, U
    Roettig, U
    Paal, R
    TETRAHEDRON LETTERS, 2001, 42 (31) : 5187 - 5189
  • [19] Synthesis of [5-(1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines
    Pokhodylo, N. T.
    Shiika, O. Ya.
    Matiichuk, V. S.
    Obushak, N. D.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (03) : 417 - 421
  • [20] BENZOTHIAZOLE DERIVATIVES .4. SYNTHESIS OF SOME 2-(1,3,4-OXADIAZOL-2-YL) AND 6-(1,3,4-OXADIAZOL-2-YL) BENZOTHIAZOLES AND 2-(1,3,4-THIADIAZOL-2-YL) AND 6-(1,3,4-THIADIAZOL-2-YL) BENZOTHIAZOLES AS POTENTIAL ANTIINFLAMMATORY AGENTS
    SAWHNEY, SN
    SINGH, J
    BANSAL, OP
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1974, 51 (10) : 886 - 890