Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes in the Superbasic System NaOH/DMSO

被引:6
作者
Shetnev, A. A. [1 ]
Pankratieva, V. E. [2 ]
Kunichkina, A. S. [2 ]
Vlasov, A. S. [1 ]
Proskurina, I. K. [2 ]
Kotov, A. D. [2 ]
Korsakov, M. K. [1 ]
机构
[1] Ushinsky Yaroslavl State Pedag Univ, Dorogov Pharmaceut Technol Transfer Ctr, Yaroslavl 150000, Russia
[2] Ushinsky Yaroslavl State Pedag Univ, Yaroslavl 150000, Russia
基金
俄罗斯基础研究基金会;
关键词
aldehyde; amidoxime; oxadiazole; superbasic medium; condensation; dimethyl sulfoxide; sodium hydroxide; ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; NITRILE OXIDE; DERIVATIVES; EFFICIENT; ACIDS; CYCLIZATION; INHIBITORS; PERIPHERY; FACILE;
D O I
10.1134/S107042802007009X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new procedure has been proposed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with aldehydes in the superbasic system NaOH/DMSO at room temperature. The scope of the proposed procedure has been demonstrated by 15 syntheses from various amidoximes and aromatic aldehydes with 27-76% yields. The procedure is inapplicable to aliphatic aldehydes.
引用
收藏
页码:1181 / 1186
页数:6
相关论文
共 35 条
[1]   Microwave-assisted efficient, one-pot, three-component synthesis of 3,5-disubstituted 1,2,4-oxadiazoles under solvent-free conditions [J].
Adib, M ;
Jahromi, AH ;
Tavoosi, N ;
Mahdavi, M ;
Bijanzadeh, HR .
TETRAHEDRON LETTERS, 2006, 47 (17) :2965-2967
[2]   One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate [J].
Amarasinghe, Kande K. D. ;
Maier, Matthew B. ;
Srivastava, Anil ;
Gray, Jeffrey L. .
TETRAHEDRON LETTERS, 2006, 47 (22) :3629-3631
[3]   PTSA-ZnCl2: An Efficient Catalyst for the Synthesis of 1,2,4-Oxadiazoles from Amidoximes and Organic Nitriles [J].
Augustine, John Kallikat ;
Akabote, Vani ;
Hegde, Shrivatsa Ganapati ;
Alagarsamy, Padma .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5640-5643
[4]   The reaction of amidoximes with carboxylic acids or their esters under high-pressure conditions [J].
Baikov, S., V ;
Stashina, G. A. ;
Chernoburova, E., I ;
Krylov, V. B. ;
Zavarzin, I., V ;
Kofanov, E. R. .
RUSSIAN CHEMICAL BULLETIN, 2019, 68 (02) :347-350
[5]   The first one-pot ambient-temperature synthesis of 1,2,4-oxadiazoles from amidoximes and carboxylic acid esters [J].
Baykov, Sergey ;
Sharonova, Tatyana ;
Shetnev, Anton ;
Rozhkov, Sergey ;
Kalinin, Stanislav ;
Smirnov, Alexey V. .
TETRAHEDRON, 2017, 73 (07) :945-951
[6]   A convenient and mild method for 1,2,4-oxadiazole preparation: cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO [J].
Baykov, Sergey ;
Sharonova, Tatyana ;
Osipyan, Angelina ;
Rozhkoy, Sergey ;
Shetnev, Anton ;
Smirnov, Alexey .
TETRAHEDRON LETTERS, 2016, 57 (26) :2898-2900
[7]   Unprecedented stereoselective synthesis of 3-methylisoxazolidine-5-aryl-1,2,4-oxadiazoles via 1,3-dipolar cycloaddition and study of their in vitro antioxidant activity [J].
Brahmi, Jihed ;
Ghannay, Siwar ;
Bakari, Sana ;
Aouadi, Kaiss ;
Kadri, Adel ;
Msaddek, Moncef ;
Vidal, Sebastien .
SYNTHETIC COMMUNICATIONS, 2016, 46 (24) :2037-2044
[8]   Parallel synthesis of 1,2,4-oxadiazoles using CDI activation [J].
Deegan, TL ;
Nitz, TJ ;
Cebzanov, D ;
Pufko, DE ;
Porco, JA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (02) :209-212
[9]   NITRILE OXIDE CYCLOADDITION ROUTES TO 2-(ISOXAZOLYL)-BENZOATES AND 2-(1,2,4-OXADIAZOL-3-YL)BENZOATES [J].
HOWE, RK ;
SCHLEPPNIK, FM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (04) :721-726
[10]   A novel synthesis of 1,2,4-oxadiazoles and isoxazoles [J].
Kivrak, Arif ;
Zora, Metin .
TETRAHEDRON, 2014, 70 (04) :817-831