The Reaction of (N-isocyanimino) triphenylphosphorane with an Electron-poor α-Haloketone in the Presence of Aromatic Carboxylic Acids: A Novel Three-Component Reaction for the Synthesis of Disubstituted 1,3,4-oxadiazole Derivatives

被引：80
作者：
Ramazani, Ali [1 ]
Ahmadi, Yavar [1 ]
Rouhani, Morteza [1 ]
Shajari, Nahid [1 ]
Souldozi, Ali [2 ]
机构：
[1] Zanjan Univ, Dept Chem, Zanjan, Iran
[2] Islamic Azad Univ Urmia Branch, Dept Chem, Orumiyeh, Iran
来源：
HETEROATOM CHEMISTRY | 2010年 / 21卷 / 06期
基金：
美国国家科学基金会;
关键词：
ONE-POT SYNTHESIS; POLYMER-SUPPORTED REAGENTS; (N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE; MILD;
D O I：
10.1002/hc.20626
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reactions of electron-poor alpha-haloketones with (N-isocyanimino) triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and in neutral conditions to afford disubstituted 1,3,4-oxadiazole derivatives in high yields. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:368-372, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20626
引用
收藏
页码：368 / 372
页数：5
相关论文
共 32 条
[1]   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
[2]   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
[3]   Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions [J].
Brain, CT ;
Paul, JM ;
Loong, Y ;
Oakley, PJ .
TETRAHEDRON LETTERS, 1999, 40 (16) :3275-3278
[4]   Synthesis of 1,3,4-oxadiazoles using polymer-supported reagents [J].
Brain, CT ;
Brunton, SA .
SYNLETT, 2001, (03) :382-384
[5]  
Brown BJ, 2000, SYNLETT, P131
[6]   IMPROVED FISCHER INDOLE REACTION FOR THE PREPARATION OF N,N-DIMETHYLTRYPTAMINES - SYNTHESIS OF L-695,894, A POTENT 5-HT1D RECEPTOR AGONIST [J].
CHEN, CY ;
SENANAYAKE, CH ;
BILL, TJ ;
LARSEN, RD ;
VERHOEVEN, TR ;
REIDER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3738-3741
[7]   Synthesis, structure, and transformation of novel osmium azine and ylide complexes [J].
Chiu, TW ;
Liu, YH ;
Chi, KM ;
Wen, YS ;
Lu, KL .
INORGANIC CHEMISTRY, 2005, 44 (18) :6425-6430
[8]   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
[9]   Synthesis of 2-aryl-1,2,3,4-tetrahydroquinazolin-1-ols and their conversion to 7-aryl-9H-6-oxa-5,8-diaza-benzocycloheptenes [J].
Coskun, N ;
Çetin, M .
TETRAHEDRON LETTERS, 2004, 45 (49) :8973-8975
[10]   THE CHEMISTRY OF PSEUDOMONIC ACID .10. PREPARATION OF HETEROCYCLIC-DERIVATIVES [J].
CRIMMIN, MJ ;
OHANLON, PJ ;
ROGERS, NH ;
WALKER, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :2047-2057
1234