One-Pot Efficient Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, Carboxylic Acids, and Aromatic Bis-Aldehydes

被引:29
作者
Ramazani, Ali [1 ]
Ahmadi, Yavar [2 ]
Mahyari, Amir [1 ]
机构
[1] Zanjan Univ, Dept Chem, Zanjan, Iran
[2] Islamic Azad Univ, Zanjan, Iran
基金
美国国家科学基金会;
关键词
Aromatic carboxylic acid; aza-Wittig reaction; heteroaromatic carboxylic acid; (N-isocyanimino)triphenylphosphorane; 1; 3; 4-oxadiazole; STABILIZED PHOSPHORUS YLIDES; POLYMER-SUPPORTED REAGENTS; SINGLE-CRYSTAL STRUCTURE; N-VINYLIC PHOSPHAZENES; AZA-WITTIG REACTION; X-RAY-STRUCTURE; STEREOSELECTIVE-SYNTHESIS; 3-COMPONENT REACTION; SILICA-GEL; ACETYLENIC ESTERS;
D O I
10.1080/00397911.2010.501480
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[image omitted] Reactions of (N-isocyanimino)triphenylphosphorane with aromatic bis-aldehydes (isophthalaldehyde and terphthalaldehyde) in the presence of aromatic (or heteroaromatic) carboxylic acids proceed smoothly at room temperature and in neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in good yields. The reaction proceeds smoothly and cleanly under mild conditions, and no side reactions were observed.
引用
收藏
页码:2273 / 2282
页数:10
相关论文
共 49 条
[1]   Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino) phenyl]acetic acid derivatives [J].
Amir, M ;
Shikha, K .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (06) :535-545
[2]  
[Anonymous], 1995, PHOSPHORUS OUTLINE C
[3]   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
[4]   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
[5]   Synthesis, antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives [J].
Chen, Qiong ;
Zhu, Xiao-Lei ;
Jiang, Li-Li ;
Liu, Zu-Ming ;
Yang, Guang-Fu .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) :595-603
[6]   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
[7]   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
[8]   Mechanism and stereoselectivity of the aza-Wittig reaction between phosphazenes and aldehydes [J].
Cossío, FP ;
Alonso, C ;
Lecea, B ;
Ayerbe, M ;
Rubiales, G ;
Palacios, F .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (07) :2839-2847
[9]   Triphenylphosphine-Catalyzed Preparation of Sterically Congested, Electron-Poor N-Vinylimidazole Derivatives from Acetylenic Esters and Imidazole-Containing NH-Acids [J].
Farshadi, Azam ;
Ramazani, Ali ;
Mahyari, Amir Tofangchi ;
Khoobi, Mehdi ;
Ahmadi, Yavar ;
Nasrabadi, Fatemeh Zeinali .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (12) :2489-2495
[10]   Ring closure reactions in heterocyclic systems with implementation of Wittig and aza-Wittig reactions [J].
Hajos, Gyorgy ;
Nagy, Ildiko .
CURRENT ORGANIC CHEMISTRY, 2008, 12 (01) :39-58