Green oxidative cyclization to access 2,5-disubstituted-1,3,4-oxadiazoles from aldehydes and hydrazide derivatives using FeBr3 catalyst and hydrogen peroxide

被引：2

作者：

Wang, Jian ^{[1
]}

Wang, Linyang ^{[2
]}

Qin, Huilin ^{[2
]}

Tian, Ruotong ^{[2
]}

Pan, Yuliang ^{[2
]}

机构：

[1] Fujian Normal Univ, Coll Chem & Mat Sci, Fuzhou 350007, Peoples R China

[2] Taizhou Univ, Sch Pharmaceut Sci, Taizhou 318000, Peoples R China

来源：

TETRAHEDRON LETTERS | 2023年 / 131卷

关键词：

Oxidative Cyclization; Iron(III) bromide catalyst; Hydrogen peroxide; ONE-POT SYNTHESIS; N-ACYLHYDRAZONES; 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES; OXADIAZOLES; RALTEGRAVIR; HYDRAZONES; INHIBITORS; ACIDS;

D O I：

10.1016/j.tetlet.2023.154783

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,5-disubstituted-1,3,4-oxadiazoles Oxidative cyclization of aldehydes and hydrazide derivatives to access 2,5disubstituted-1,3,4-oxadiazoles has been developed using a catalytic amount of FeBr3 in the presence of aqueous hydrogen peroxide as an oxidant. By synthesizing 35 examples of 2,5-disubstituted 1,3,4-oxadiazoles, this approach was demonstrated to have good features including broad scope, mild conditions, air/water tolerance, and simple operation. More importantly, it can be expected to find wide applications in organic synthesis.

引用

页数：5

共 36 条

[21] A Novel, One-Pot Synthesis of 2,5-Disubstituted-1,3,4-Oxadiazoles Using 1,4-Bis(Triphenylphosphonium)-2-Butene Peroxodisulfate
Badri, Rashid
Gorjizadeh, Maryam
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (03) : 544 - 549
[22] Synthesis, spectral analysis, antibacterial, antifungal, antioxidant and hemolytic activity studies of some new 2,5-disubstituted-1,3,4-oxadiazoles
Dhonnar, Sunil L.
More, Rahul A.
Adole, Vishnu A.
Jagdale, Bapu S.
Sadgir, Nutan, V
Chobe, Santosh S.
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1253
[23] Mild Oxidative Cyclization of Sydnone-Benzoylhydrazone with Lead Oxide to 2,5-Disubstituted-1,3,4-Oxadiazole-Sydnone Hybrid Derivatives
Chiang, Kuo-Chen
Wong, Fung Fuh
Hung, Chih-Hao
Huang, Yu-Ying
Chang, Po-Wei
Liao, Yang-Ming
Lin, Shao-Kai
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (01) : 111 - 115
[24] A green one-pot process for the synthesis of 1,2,4-triazole-fused heterocycles using FeBr3 catalyst and hydrogen peroxide
Pan, Yuliang
Tian, Ruotong
Chen, Yini
Wang, Linyang
Qin, Huilin
Wang, Jian
TETRAHEDRON, 2023, 148
[25] 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):
[26] Synthesis of 1,3,4-Oxadiazoles from 1,2-Diacylhydrazines Using SO 2 F 2 as a Simple and Practical Cyclization Reagent
Chen, Jingao
Lou, Zhengzheng
Jin, Hongxuan
Ding, Chengrong
Zhang, Guofu
SYNLETT, 2025,
[27] Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions
Lu, Fangling
Gong, Fengping
Li, Liangsen
Zhang, Kan
Li, Zhen
Zhang, Xinwei
Yin, Ying
Wang, Ying
Gao, Ziwei
Zhang, Heng
Lei, Aiwen
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (22) : 3257 - 3260
[28] Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated decarboxylation-cyclization of hydrazides and diketones
Diao, Pinhui
Ge, Yanqin
Zhang, Wenpei
Xu, Chen
Zhang, Nannan
Guo, Cheng
TETRAHEDRON LETTERS, 2018, 59 (08) : 767 - 770
[29] Efficient oxidative cyclisation of acid hydrazides to 2,5-disubstituted 1,3,4-oxadiazoles catalysed by Bu4NI with t-BuOOH as oxidant
Gao, Peng
Wei, Yunyang
JOURNAL OF CHEMICAL RESEARCH, 2013, (08) : 506 - 510
[30] Oxidative cyclization of N-aroylhydrazones to 2-(2-arylethenyl)-1,3,4-oxadiazoles using DDQ as an efficient oxidant
Jasiak, Karolina
Kudelko, Agnieszka
TETRAHEDRON LETTERS, 2015, 56 (43) : 5878 - 5881

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