Microwave promoted one-pot synthesis of 2-aryl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazole derivatives using Al3+-K10 clay as a heterogeneous catalyst

被引:30
作者
Suresh, Dhanusu [1 ]
Kanagaraj, Kuppusamy [1 ]
Pitchumani, Kasi [1 ,2 ]
机构
[1] Madurai Kamaraj Univ, Sch Chem, Madurai 625021, Tamil Nadu, India
[2] Madurai Kamaraj Univ, Sch Chem, Ctr Green Chem, Madurai 625021, Tamil Nadu, India
关键词
K10-montmorillonite; 1,3,4-Oxadiazoles; 1,2,4-Oxadiazoles; One-pot solvent-free synthesis; Green protocol; POLYMER-SUPPORTED REAGENTS; ONE-STEP SYNTHESIS; SOLVENT-FREE; EFFICIENT; INHIBITORS; ACID; DISCOVERY; ZEOLITE; DESIGN;
D O I
10.1016/j.tetlet.2014.05.004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, inexpensive method is developed for the one-pot synthesis of 2-aryl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazoles starting from acid hydrazides and trimethyl orthoformate under solvent-free, microwave conditions using a reusable Al3+-K10 montmorillonite clay as a heterogeneous catalyst. The novelty of the present study lies in the synthesis of oxadiazole and benzimidazole moieties in a onepot process in high yield from easily available precursors and catalysts under mild conditions. [GRAPHICS] (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3678 / 3682
页数:5
相关论文
共 46 条
[1]   THE CONDENSATION OF ARYL CARBOXYLIC ACID HYDRAZIDES WITH ORTHOESTERS [J].
AINSWORTH, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (05) :1148-1150
[2]  
Alegaon S G., 2011, EUR J CHEM, V2, P94, DOI [10.5155/eurjchem.2.1.94-99.161, DOI 10.5155/EURJCHEM.2.1.94-99.161]
[3]   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
[4]   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
[5]   P2-P3 conformationally constrained ketoamide-based inhibitors of cathepsin K [J].
Barrett, DG ;
Boncek, VM ;
Catalano, JG ;
Deaton, DN ;
Hassell, AM ;
Jurgensen, CH ;
Long, ST ;
McFadyen, RB ;
Miller, AB ;
Miller, LR ;
Payne, JA ;
Ray, JA ;
Samano, V ;
Shewchuk, LM ;
Tavares, FX ;
Wells-Knecht, KJ ;
Willard, DH ;
Wright, LL ;
Zhou, HQQ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (15) :3540-3546
[6]   The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating [J].
Baxendale, IR ;
Ley, SV ;
Martinelli, M .
TETRAHEDRON, 2005, 61 (22) :5323-5349
[7]   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
[8]   Synthesis and antitumor evaluation of some new 1,3,4-oxadiazole-based heterocycles [J].
Bondock, Samir ;
Adel, Shymaa ;
Etman, Hassan A. ;
Badria, Farid A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 48 :192-199
[9]   Discovery of small molecules that enhance astrocyte differentiation in rat fetal neural stem cells [J].
Chang, Dong Jo ;
Jeong, Mi Young ;
Song, Jiho ;
Jin, Chang Yun ;
Suh, Young-Ger ;
Kim, Hyun-Jung ;
Min, Kyung Hoon .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (23) :7050-7053
[10]   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