Four-component synthesis of 1,3,4-oxadiazole derivatives from (n-isocyanimino)triphenylphosphorane, (e)-cinnamic acids, acetaldehyde and secondary amines

被引：0
|
作者：
Ramazania A. [1 ]
Ahmadi Y. [2 ]
Nasrabadi F.Z. [3 ]
机构：
[1] Chemistry Department, Islamic Azad University, Zanjan Branch, Zanjan
[2] Islamic Azad University, Zanjan Branch, Young Researchers Club, Zanjan
[3] Chemistry Department, Zanjan University, Zanjan
来源：
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences | 2011年 / 66卷 / 02期
关键词：
(E)-Cinnamic Acid; 1; 3; 4-Oxadiazole; Acetaldehyde; Aza-Wittig Reaction; N-Isocyanimino)triphenylphosphorane; Secondary Amine;
D O I：
10.1515/znb-2011-0211
中图分类号：
学科分类号：
摘要：
The 1 : 1 iminium intermediate, generated by the addition of a secondary amine to acetaldehyde is trapped by the (N-isocyanimino)triphenylphosphorane in the presence of an (E)-cinnamic acid derivative, leading to the formation of the corresponding iminophosphorane intermediate. Disubstituted 1,3, 4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediates. The reactions were completed under neutral conditions at room temperature, and the corresponding disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields. © 2011 Verlag der Zeitschrift für Naturforschung, Tübingen.
引用
收藏
页码：184 / 190
页数：6
相关论文
共 50 条
  • [41] N-isocyaniminotriphenylphosphorane (Ph3PNNC) as an efficient reagent for the synthesis of ferrocene-containing 1,3,4-oxadiazole derivatives
    Ramazani, Ali
    Fattahi, Nadia
    Ashtari, Mona
    Rezaei, Aram
    Joo, Sang Woo
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (06) : 908 - 912
  • [42] SYNTHESIS OF 5-MERCAPTOACETYL-N-ARYLUREIDO-1,3,4-OXADIAZOLE AND 1,2,4-TRIAZOLE DERIVATIVES AS POTENTIAL PESTICIDES
    GUPTA, AKS
    BAJAJ, OP
    MD, M
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1978, 16 (07): : 629 - 631
  • [43] 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
  • [44] Synthesis of N-substituted acetamide derivatives of azinane-bearing 1,3,4-oxadiazole nucleus and screening for antibacterial activity
    Iqbal, J.
    Aziz-ur-Rehman
    Abbasi, M. A.
    Siddiqui, S. Z.
    Rasool, S.
    Nafeesa, K.
    Khan, S. G.
    Shah, S. A. A.
    TROPICAL JOURNAL OF PHARMACEUTICAL RESEARCH, 2017, 16 (02) : 429 - 437
  • [45] Synthesis, Molecular Properties Prediction, and Anti-staphylococcal Activity of N-Acylhydrazones and New 1,3,4-Oxadiazole Derivatives
    de Oliveira, Cledualdo Soares
    Lira, Bruno Freitas
    Falcao-Silva, Vivyanne dos Santos
    Siqueira-Junior, Jose Pinto
    Barbosa-Filho, Jose Maria
    de Athayde-Filho, Petronio Filgueiras
    MOLECULES, 2012, 17 (05): : 5095 - 5107
  • [46] Synthesis, Therapeutic Potential, Quantum Studies and Molecular Properties of Amino Acid Fused 1,3,4-Oxadiazole Derivatives as an Unnatural Amino Acids
    Bisht, Ajay Singh
    Juyal, Divya
    INDIAN JOURNAL OF PHARMACEUTICAL EDUCATION AND RESEARCH, 2024, 58 (03) : s1075 - s1082
  • [47] Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4-Oxadiazole/1,3,4-Oxadiazoline and 1,2,4-Triazole Derivatives from N-Substituted Hydrazides
    Kotipalli, Trimurtulu
    Kavala, Veerababurao
    Konala, Ashok
    Janreddy, Donala
    Kuo, Chu-Wei
    Yao, Ching-Fa
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (16) : 2652 - 2660
  • [48] Rational design, synthesis and biological evaluation of 1,3,4-oxadiazole pyrimidine derivatives as novel pyruvate dehydrogenase complex E1 inhibitors
    He, Haifeng
    Wang, Wei
    Zhou, Yuan
    Xia, Qin
    Ren, Yanliang
    Feng, Jiangtao
    Peng, Hao
    He, Hongwu
    Feng, Lingling
    BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (08) : 1879 - 1888
  • [49] Synthesis of N-Methylmorpholinium Derivatives Possessing a 1,3,4-Oxadiazole Core as Feasible Antibacterial Agents against Plant Bacterial Diseases
    Tuo, Xinxin
    Yang, Jie
    Zhang, Yedong
    Wang, Peiyi
    JOURNAL OF CHEMISTRY, 2021, 2021
  • [50] Synthesis of 1,3,4-oxadiazole derivatives from α-amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions
    Dornelles, Luciano
    Rodrigues, Oscar E. D.
    Heck, Elisiane F.
    Bender, Caroline R.
    Cansian, Mariane B.
    Schwab, Ricardo S.
    Severo Filho, Wolmar A.
    ARKIVOC, 2015, : 131 - 144
12345