A novel four-component reaction for the synthesis of disubstituted 1,3,4-oxadiazole derivatives

被引：85
作者：
Ramazani, Ali [1 ]
Shajari, Nahid [1 ]
Mahyari, Amir [1 ]
Ahmadi, Yavar [1 ]
机构：
[1] Zanjan Univ, Dept Chem, Zanjan, Iran
来源：
MOLECULAR DIVERSITY | 2011年 / 15卷 / 02期
基金：
美国国家科学基金会;
关键词：
(N-isocyanimino)triphenylphosphorane; Aromatic carboxylic acid; Cyclobutanone; Benzyl amine; 1,3,4-oxadiazole; aza-Wittig reaction; 4CC; MCR; STABILIZED PHOSPHORUS YLIDES; POLYMER-SUPPORTED REAGENTS; ONE-POT; STEREOSELECTIVE-SYNTHESIS; ALKYL ISOCYANIDES; (N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE; ACID;
D O I：
10.1007/s11030-010-9275-0
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The 1:1 imine intermediate generated by the addition of benzyl amine to cyclobutanone is trapped by (N-isocyanimino)triphenylphosphorane in the presence of an aromatic carboxylic acid leads to the formation of the corresponding iminophosphorane intermediate. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives, were produced in excellent yields.
引用
收藏
页码：521 / 527
页数：7
相关论文
共 23 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]   Synthesis and antibacterial studies of a new series of 1,2-bis(1,3,4-oxadiazol-2-yl)ethanes and 1,2-bis(4-amino-1,2,4-triazol-3-yl)ethanes [J].
Holla, BS ;
Gonsalves, R ;
Shenoy, S .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (02) :267-271
[3]   Chemo- and stereoselective reaction between alkyl isocyanides and dimethyl 1,3-acetonedicarbocxylate in the presence of acetylenic esters [J].
Nasiri, Farogh ;
Nazem, Fatemeh ;
Pourdavaie, Kourosh .
MOLECULAR DIVERSITY, 2007, 11 (02) :101-105
[4]   One-pot synthesis of fluorine-containing alkenes from in situ-generated stabilized phosphorus ylides [J].
Pakravan, Parvaneh ;
Ramazani, Ali ;
Noshiranzadeh, Nader ;
Sedrapoushan, Alireza .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (03) :545-549
[5]   Synthetic Applications of Intramolecular Aza-Wittig Reaction for the Preparation of Heterocyclic Compounds [J].
Palacios, Francisco ;
Aparicio, Domitila ;
Rubiales, Gloria ;
Alonso, Concepcion ;
de los Santos, Jesus M. .
CURRENT ORGANIC CHEMISTRY, 2009, 13 (08) :810-828
[6]   One-pot, three-component synthesis of dialkyl 1,2-dihydroquinoline-2,3-dicarboxylates from triphenylphosphine, acetylenic esters, and amide derivatives of 2-aminobenzaldehyde in aqueous acetone [J].
Ramazani, A ;
Ahmadi, E ;
Kazemizadeh, AR ;
Dolatyari, L ;
Noshiranzadeh, N ;
Eskandari, I ;
Souldozi, A .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (11) :2419-2422
[7]   A facile synthetic approach to dimethyl 2-arylamino-3-(triphenylphosphoranylidene) succinates from electron-poor primary arylamines [J].
Ramazani, A ;
Shajari, N ;
Gouranlou, F .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2001, 174 :223-227
[8]   One-pot, four-component synthesis of dialkyl [indane-1,3-dione2-ylidene]alkoxysuccinates [J].
Ramazani, A ;
Bodaghi, A .
TETRAHEDRON LETTERS, 2000, 41 (04) :567-568
[9]   Dipotassium hydrogen phosphate-catalyzed synthesis of dialkyl 2-(4-fluoro-phenoxy)-2-butendioates from stabilized phosphorus ylides in solvent-free conditions [J].
Ramazani, Ali ;
Rahimifard, Mahshid ;
Noshiranzadeh, Nader ;
Souldozi, Ali .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (02) :413-417
[10]   Silica-gel catalyzed stereoselective conversion of stabilized phosphorus ylides to dialkyl (Z)-2-(2-methoxycarbonyl-phenoxy)-2-butenedioates in solvent-free conditions [J].
Ramazani, Ali ;
Rahimifard, Mahshid ;
Souldozi, Ali .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (01) :1-5
123