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 50 条
  • [31] N-Isocyaniminotriphenylphosphorane (Ph3PNNC) as an Efficient Reagent for the Synthesis of Fully Substituted 1,3,4-Oxadiazoles from 3-Phenyl-2-Propynoic Acid, Secondary Amines and Aromatic Bis-Aldehydes
    Ahankar, Hamideh
    Ramazani, Ali
    Ahmadi, Yavar
    Amini, Issa
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2013, 188 (07) : 886 - 894
  • [32] Tetrabutylammonium Iodide-Mediated One-Pot Construction of 1,3,4-Oxadiazole Derivatives with Alkyl Amide and Hydrazine
    Jing, Zhixia
    Du, Jianxi
    Jiang, Ping
    Ablajan, Keyume
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (11) : 3930 - 3938
  • [33] One-pot Synthesis of a 3,4,5-Triaryltriazole from the Subsitituted 1,3,4-Oxadiazole: Crystal Structures Characterization
    Jiang, Jing-Jing
    Shen, Guo-Ping
    He, Xin
    Shen, Xuan
    Zhu, Dun-Ru
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (06) : 1888 - 1892
  • [34] An efficient one-pot synthesis of N-methoxy-N-methylamides from carboxylic acids
    Kim, M
    Lee, H
    Han, KJ
    Kay, KY
    SYNTHETIC COMMUNICATIONS, 2003, 33 (23) : 4013 - 4018
  • [35] The Reaction of (N-Isocyanimino) triphenylphosphorane with (E)-3-Aryl-2-propenoic Acid Derivatives: One-Pot Synthesis of 2-[(E)-2-Aryl-1-ethenyl]-1,3,4-oxadiazoles via Intramolecular aza-Wittig Reaction
    Ahankar, Hamideh
    Ramazani, Ali
    Amini, Issa
    Ahmadi, Yavar
    Souldozi, Ali
    HETEROATOM CHEMISTRY, 2011, 22 (05) : 612 - 616
  • [36] Y(OTf)3-catalyzed, one-pot synthesis of 1,2,4-oxadiazole derivatives
    Yu, Chuanming
    Lei, Min
    Su, Weike
    Xie, Yuanyuan
    SYNTHETIC COMMUNICATIONS, 2007, 37 (22-24) : 4439 - 4452
  • [37] (N-Isocyanimino)triphenylphosphorane-Mediated, One-Pot, Efficient Synthesis of Sterically Congested 1,1,1-Trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2-propanol Derivatives via Intramolecular Aza-Wittig Reaction
    Ramazani, Ali
    Shajari, Nahid
    Mahyari, Amir Tofangchi
    Khoobi, Mehdi
    Ahmadi, Yavar
    Souldozi, Ali
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (12) : 2496 - 2502
  • [38] Efficient one-pot, four-component synthesis of N,N-dibenzyl-1-(5-aryl-1,3,4-oxadiazol-2-yl)cyclobutylamine derivatives from the reaction of (isocyanoimino)triphenylphosphorane, dibenzylamine, an aromatic carboxylic acid and cyclobutanone
    Shajari, Nahid
    Kazemizadeh, Ali Reza
    Ramazani, Ali
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2012, 77 (09) : 1175 - 1180
  • [39] Four-component synthesis of disubstituted 1,3,4-oxadiazole derivatives from cinnamaldehyde, an aromatic carboxylic acid, a secondary amine, and N-isocyaniminotriphenylphosphorane
    Ramazani, Ali
    Kalhor, Robabe
    Rezaei, Aram
    Karimi, Zahra
    HETEROATOM CHEMISTRY, 2012, 23 (04) : 315 - 321
  • [40] Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines
    Javanbani, Hamideh
    Ramazani, Ali
    Joo, Sang Woo
    Ahmadi, Yavar
    Azizkhani, Vahid
    Asiabi, Pegah Azimzadeh
    IRANIAN CHEMICAL COMMUNICATION, 2015, 3 (04) : 310 - 322