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

被引:40
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
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 52 条
[1]   High-efficiency organic electrophosphorescent devices with tris(2-phenylpyridine)iridium doped into electron-transporting materials [J].
Adachi, C ;
Baldo, MA ;
Forrest, SR ;
Thompson, ME .
APPLIED PHYSICS LETTERS, 2000, 77 (06) :904-906
[2]   ANTIARRHYTHMIC AGENTS SYNTHESIS AND BIOLOGICAL-ACTIVITY OF SOME TETRAZOLE AND OXADIAZOLE ANALOGS OF 4-DIALKYLAMINO-2,2-DIARYLBUTYRAMIDES [J].
ADELSTEIN, GW .
JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (04) :309-312
[3]   Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles [J].
Almasirad, A ;
Tabatabai, SA ;
Faizi, M ;
Kebriaeezadeh, A ;
Mehrabi, N ;
Dalvandi, A ;
Shafiee, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (24) :6057-6059
[4]   A CONVENIENT SYNTHESIS OF ALKYL AND ARYL SUBSTITUTED BIS-1,3,4-OXADIAZOLES [J].
ALTALIB, M ;
TASHTOUSH, H ;
ODEH, N .
SYNTHETIC COMMUNICATIONS, 1990, 20 (12) :1811-1817
[5]   Rapid synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under microwave irradiation [J].
Bentiss, F ;
Lagrenée, M ;
Barbry, D .
SYNTHETIC COMMUNICATIONS, 2001, 31 (06) :935-938
[6]   Optimization of high-performance blue organic light-emitting diodes containing tetraphenylsilane molecular glass materials [J].
Chan, LH ;
Lee, RH ;
Hsieh, CF ;
Yeh, HC ;
Chen, CT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (22) :6469-6479
[7]   A facile procedure for the one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles [J].
Dabiri, Minoo ;
Salehi, Peyman ;
Baghbanzadeh, Mostafa .
TETRAHEDRON LETTERS, 2006, 47 (39) :6983-6986
[8]   Convenient preparation of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess-Martin reagent [J].
Dobrota, Cristian ;
Paraschivescu, Codruta C. ;
Dumitru, Ioana ;
Matache, Mihaela ;
Baciu, Ion ;
Ruta, Lavinia L. .
TETRAHEDRON LETTERS, 2009, 50 (17) :1886-1888
[9]   4-OH-TEMPO/TCQ/TBN/HCl: A Metal-Free Catalytic System for Aerobic Oxidation of Alcohols under Mild Conditions [J].
Dong, Yanli ;
Zhao, Xiaomei ;
Liu, Renhua .
CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (09) :1019-1023
[10]   Synthesis and spectral characterization of novel 1,3,4-oxadiazole and 1,2,4-triazole derivatives: Synthesis for potential pharmacological activities [J].
Faidallah, HM ;
Sharshira, EM ;
Basaif, SA ;
A-Ba-Oum, AEK .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (01) :67-79