A new and efficient method for the synthesis of 2-N-(aryl)-1,3,4-oxadiazole-2,5-diamine derivatives

被引：4

作者：

Brahmayya, Manuri ^{[1
]}

Liu, Fan-Shuan ^{[1
]}

Suen, Shing-Yi ^{[1
]}

Huang, Chun-Chieh ^{[1
]}

Dai, Shenghong A. ^{[1
]}

Guo, Yi-Syuan ^{[1
]}

Chen, Yi-Fen ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem Engn, Taichung 402, Taiwan

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2016年 / 42卷 / 03期

关键词：

Cyclisation; Heterocycles; Heteroatom; Synthesis; Diamino oxadiazoles; Reaction mechanism; KINASE CDK INHIBITORS; ANTIBACTERIAL ACTIVITY; MICROWAVE IRRADIATION; AGENTS; 2-AMINO-1,3,4-OXADIAZOLES;

D O I：

10.1007/s11164-015-2128-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a series of cyclic analogues of 2,5-diamino-1,3,4-oxadiazoles which were prepared in a simple and general protocol. This method involves easy cyclisation of N-(aryl)-1,2-hydrazinedicarboxamides and mediated by tosylchloride/pyridine in ethanol (solvent) under a reflux condition (79-80 A degrees C), over a time period of 20 h. We prepared different examples in a higher range of yields (80-98 %) by using this protocol.

引用

页码：1965 / 1975

页数：11

共 36 条

[1] Synthesis, characterization and anti-bacterial activity of 5-(alkenyl)-2-amino- and 2-(alkenyl)-5-phenyl-1,3,4-oxadiazoles [J].

Banday, Mudasir R. ;

Mattoo, Rayees H. ;

Rauf, Abdul .

JOURNAL OF CHEMICAL SCIENCES, 2010, 122 (02) :177-182

[2] (+/-)-3,4,4a,5,6,7-hexahydro-4a-methyl-7,7-diphenyl-1(2H)-naphthalenone [J].

Bunce, RA ;

Childress, RS .

SYNTHETIC COMMUNICATIONS, 1996, 26 (21) :4081-4089

[3]

Chervinskii A.Y., 1983, DOKL AKAD NAUK SSSR, V273, P6

[4] Total synthesis of (-)- and ent-(+)-vindoline [J].

Choi, YG ;

Ishikawa, H ;

Velcicky, J ;

Elliott, GI ;

Miller, MM ;

Boger, DL .

ORGANIC LETTERS, 2005, 7 (20) :4539-4542

[5] Efficient one-pot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin-bound reagents [J].

Coppo, FT ;

Evans, KA ;

Graybill, TL ;

Burton, G .

TETRAHEDRON LETTERS, 2004, 45 (16) :3257-3260

[6]

David A.N., 2004, BIOORG MED CHEM LETT, V14, P5489

[7]

De la Saulnilre PC, 1942, ANN CHIM FRANCE, V17, P353

[8] Synthesis of 5-trimethylsilylethynyl-1,3,4-oxadiazoles [J].

Demina, MM ;

Sarapulova, GI ;

Borisova, AI ;

Larina, LI ;

Medvedeva, AS .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (10) :1522-1524

[9] 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

[10] Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities [J].

Dogan, HN ;

Duran, A ;

Rollas, S ;

Sener, G ;

Uysal, MK ;

Gülen, D .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (09) :2893-2898

← 1 2 3 4 →