A convenient and mild method for 1,2,4-oxadiazole preparation: cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO

被引:42
|
作者
Baykov, Sergey [1 ]
Sharonova, Tatyana [1 ]
Osipyan, Angelina [1 ]
Rozhkoy, Sergey [2 ]
Shetnev, Anton [1 ]
Smirnov, Alexey [1 ]
机构
[1] Ushinsky Yaroslavl State Pedag Univ, 108 Respublikanskaya St, Yaroslavl 150000, Russia
[2] Yaroslavl State Tech Univ Yaroslavl, 88 Moscowsky Pr, Yaroslavl 150023, Russia
关键词
1,2,4-Oxadiazoles; Cyclodehydration; Superbase system; O-Acylarnidoximes; DMSO; BIPOLAR HOST MATERIALS; HIGHLY EFFICIENT; DISCOVERY; FLUORIDE; DESIGN;
D O I
10.1016/j.tetlet.2016.05.071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we reported a general, convenient, and efficient synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO (M = Li, Na, K). Excellent isolated yields (up to 98%) were attained within short reaction times (10-20 min). In addition, mild reaction conditions and a simple work-up procedure allow the synthesis of a wide range of heat-labile 1,2,4-oxadiazole-containing substances. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2898 / 2900
页数:3
相关论文
共 37 条
  • [1] Synthesis, Antitumor and Cytotoxic Activity of New Adamantyl O-Acylamidoximes and 3-Aryl-5-Adamantane-1,2,4-Oxadiazole Derivatives
    Aguiar, Deivson Ferreira
    Alves Dutra, Luana Leticia
    Dantas, Willyenne Marilia
    Camelo de Carvalho, Guilherme Graziany
    Goncalves Lemes, Romelia Pinheiro
    Pessoa, Claudia do O.
    Koscky Paier, Carlos Roberto
    Barros Araujo, Patricia Lopes
    Araujo, Elmo Silvano
    Pena, Lindomar Jose
    de Oliveira, Ronaldo Nascimento
    [J]. CHEMISTRYSELECT, 2019, 4 (31): : 9112 - 9118
  • [2] Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: a highly efficient and fluoride-free ring closure reaction of O-acylamidoximes
    Otaka, Hiromichi
    Ikeda, Junya
    Tanaka, Daisuke
    Tobe, Masanori
    [J]. TETRAHEDRON LETTERS, 2014, 55 (05) : 979 - 981
  • [3] SIMPLE SYNTHESIS OF 1,2,4-OXADIAZOLE SYSTEM VIA N-O BOND
    GOTZ, N
    ZEEH, B
    [J]. SYNTHESIS-STUTTGART, 1976, (04): : 268 - 270
  • [4] A convenient method for the preparation of 2,5-bis-(4-aminophenyl)-1,3,4-oxadiazole
    Davis, MC
    Chafin, AP
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2004, 36 (04) : 375 - 379
  • [5] Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives
    Ispikoudi, Maria
    Amvrazis, Michalis
    Kontogiorgis, Christos
    Koumbis, Alexandros E.
    Litinas, Konstantinos E.
    Hadjipavlou-Litina, Dimitra
    Fylaktakidou, Konstantina C.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) : 5635 - 5645
  • [6] MODEL STUDIES ON THE STRUCTURE OF POLY(AMIDE OXIME)S AND THEIR CYCLODEHYDRATION REACTIONS LEADING TO POLY(1,2,4-OXADIAZOLE)S
    JUNG, JC
    PARK, SB
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1993, 31 (13) : 3351 - 3359
  • [7] PROPERTIES OF COPOLYMERS DERIVED FROM 2,5-DIMETHYLTEREPHTHALAMIDOXIME AND CYCLODEHYDRATION TO COPOLY(1,3-ARYLENE-1,2,4-OXADIAZOLE)S
    CHOI, EJ
    JUNG, JC
    [J]. POLYMER JOURNAL, 1992, 24 (01) : 121 - 125
  • [8] A novel and convenient method for the synthesis of 1,2,4-oxadiazole-5-thiones
    Kaboudin, Babak
    Soleymanie, Saman
    Sabzalipour, Ali
    Kazemi, Foad
    Fukaya, Haruhiko
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024,
  • [9] A convenient synthesis of 5-amino-substituted 1,2,4-oxadiazole derivatives via reactions of amidoximes with carbodiimides
    Ispikoudi, Maria
    Litinas, Konstantinos E.
    Fylaktakidou, Konstantina C.
    [J]. HETEROCYCLES, 2008, 75 (06) : 1321 - 1328
  • [10] Preparation of 3-aryl-5-phenylselenomethyl 1,2,4-oxadiazole and their further deselenenylation reaction
    Xu, WM
    Miao, MZ
    Xu, RF
    Huang, X
    [J]. CHINESE CHEMICAL LETTERS, 2005, 16 (07) : 909 - 910