Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

被引：39
|
作者：
Zhang, Guofu [1 ]
Yu, Yidong [1 ]
Zhao, Yiyong [1 ]
Xie, Xiaoqiang [1 ]
Ding, Chengrong [1 ]
机构：
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
来源：
SYNLETT | 2017年 / 28卷 / 11期
基金：
中国国家自然科学基金;
关键词：
oxadiazoles; iron catalysis; cyclization; oxidation; aroyl hydrazones; ONE-POT SYNTHESIS; N-ACYLHYDRAZONES; DERIVATIVES; ACIDS; OPTIMIZATION; OXADIAZOLES; HYDRAZONES; LIGANDS; DEVICES; ANALOGS;
D O I：
10.1055/s-0036-1588747
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O-2.
引用
收藏
页码：1373 / 1377
页数：5
相关论文
共 50 条
  • [31] Synthesis and biological activity of novel 2,5-disubstituted-1,3,4-oxadiazoles
    Shailaja, M.
    Anitha, M.
    Manjula, A.
    Rao, B. Vittal
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2010, 49 (08): : 1088 - 1097
  • [32] Polyethylene glycol (PEG) mediated green synthesis of 2,5-disubstituted 1,3,4-oxadiazoles catalyzed by ceric ammonium nitrate (CAN)
    Kidwai, Mazaahir
    Bhatnagar, Divya
    Mishra, Neeraj Kumar
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (01) : 55 - 59
  • [33] N-Heterocyclic Carbene-Catalyzed Cyclization of Aldehydes with α-Diazo Iodonium Triflate: Facile Access to 2,5-Disubstituted 1,3,4-Oxadiazoles
    Huang, Hang
    Zou, Xianghua
    Cao, Si
    Peng, Zhihong
    Peng, Yingying
    Wang, Xi
    ORGANIC LETTERS, 2021, 23 (11) : 4185 - 4190
  • [34] An efficient approach to access 2,5-disubstituted 1,3,4-oxadiazoles by oxidation of 2-arenoxybenzaldehyde N-acyl hydrazones with molecular iodine
    Kucuk, Hatice Baspinar
    Alhonaish, Anoud
    Yildiz, Tulay
    Guzel, Mustafa
    CHEMISTRYSELECT, 2022, 7 (26):
  • [35] Synthesis and biological evaluation of some new 2,5-disubstituted 1,3,4-oxadiazoles from 3-(arylsulfonyl) propanehydrazides
    Kumar, L. Vinay
    Naik, P. Jagan
    Naveen, M.
    Chandrasekhar, T.
    Reddy, A. Babul
    Penchalaiah, N.
    Swamy, G. Narayana
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2014, 53 (02): : 208 - 211
  • [36] Synthesis, Antiinflammatory and Antiimicrobial Activity of Some 2,5-Disubstituted-1,3,4-oxadiazoles
    Das, Rina
    Mehta, Dinesh Kumar
    ASIAN JOURNAL OF CHEMISTRY, 2009, 21 (06) : 4419 - 4424
  • [37] Synthesis and Antimicrobial Activity of New 2,5-Disubstituted 1,3,4-Oxadiazoles and 1,2,4-Triazoles and Their Sugar Derivatives
    El-Sayed, Wael A.
    Ali, Omar M.
    Hendy, Hend A.
    Abdel-Rahman, Adel A. H.
    CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (01) : 77 - 83
  • [38] 10-Camphorsulfonic acid ((±)-CSA) catalyzed facile one-pot synthesis of a new class of 2,5-disubstituted 1,3,4-oxadiazoles
    Mule, Siva Nagi Reddy
    Battula, Sailaja Kumari
    Velupula, Ganapathi
    Guda, Dinneswara Reddy
    Bollikolla, Hari Babu
    RSC ADVANCES, 2014, 4 (102): : 58397 - 58403
  • [39] Synthesis of 1,3,4-Oxadiazoles by Iodine-Mediated Oxidative Cyclization of Methyl Ketones with 4-Phenylsemicarbazide
    Zhang, Shanshan
    Liu, Chuang
    Wu, Xiaojun
    Li, Wen
    Li, He
    Wang, Shiwei
    Leng, Yuting
    Wu, Yangjie
    SYNLETT, 2022, 33 (03) : 269 - 272
  • [40] 3D-QSAR modeling and molecular docking studies on a series of 2,5 disubstituted 1,3,4-oxadiazoles
    Ghaleb, Adib
    Aouidate, Adnane
    Ghamali, Mounir
    Sbai, Abdelouahid
    Bouachrine, Mohammed
    Lakhlifi, Tahar
    JOURNAL OF MOLECULAR STRUCTURE, 2017, 1145 : 278 - 284
12345