Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from alpha-Keto Acids and Acylhydrazines Under Mild Conditions

作者:Lu, FL (Lu, Fangling)[ 1 ] ; Gong, FP (Gong, Fengping)[ 2 ] ; Li, LS (Li, Liangsen)[ 2 ] ; Zhang, K (Zhang, Kan)[ 1 ] ; Li, Z (Li, Zhen)[ 2 ] ; Zhang, XW (Zhang, Xinwei)[ 2 ] ; Yin, Y (Yin, Ying)[ 2 ] ; Wang, Y (Wang, Ying)[ 2 ] ; Gao, ZW (Gao, Ziwei)[ 1 ] ; Zhang, H (Zhang, Heng)[ 3 ] ; Lei, AW (Lei, Aiwen)[ 2,3 ]

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

卷: 2020 期: 22 页: 3257-3260

DOI: 10.1002/ejoc.202000311

出版年: JUN 16 2020

在线发表日期: MAY 2020

文献类型:Article

摘要

1,3,4-Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between alpha-keto acids and acylhydrazines has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.

关键词

作者关键词:Electrocatalysis; Heterocycles; Oxadiazoles; Synthetic methods

KeyWords Plus:ONE-POT SYNTHESIS; OXOCARBOXYLIC ACIDS; DECARBOXYLATIVE ACYLATION; PHOTOREDOX CATALYSIS; FACILE ACCESS; GREEN; ELECTROSYNTHESIS; ENAMINONES; REAGENTS; INDOLES

作者信息

通讯作者地址:

Shaanxi Normal University Shaanxi Normal Univ Xian, Coll Chem & Chem Engn, Xian 710119, Peoples R China.

Jiangxi Normal University Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China.

Wuhan University Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Hubei, Peoples R China.

通讯作者地址: Gao, ZW (通讯作者)

Shaanxi Normal Univ Xian, Coll Chem & Chem Engn, Xian 710119, Peoples R China.

通讯作者地址: Lei, AW (通讯作者)

Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China.

通讯作者地址: Zhang, H; Lei, AW (通讯作者)

Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Hubei, Peoples R China.

地址:

[ 1 ]‎ Shaanxi Normal Univ Xian, Coll Chem & Chem Engn, Xian 710119, Peoples R China

[ 2 ]‎ Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China

[ 3 ]‎ Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Hubei, Peoples R China

电子邮件地址:zwgao@snnu.edu.cn; hengzhang@whu.edu.cn; aiwenlei@whu.edu.cn