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

页码：184 / 190

页数：6

共 50 条

[1] Four-component Synthesis of 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, (E)-Cinnamic Acids, Acetaldehyde and Secondary Amines
Ramazani, Ali
Ahmadi, Yavar
Nasrabadi, Fatemeh Zeinali
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2011, 66 (02): : 184 - 190
[2] Synthesis of sterically congested 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, acenaphthoquinone, and (N-isocyanimino)triphenylphosphorane
Ali Ramazani
Fatemeh Zeinali Nasrabadi
Asemeh Mashhadi Malekzadeh
Yavar Ahmadi
Monatshefte für Chemie - Chemical Monthly, 2011, 142
[3] Synthesis of sterically congested 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, acenaphthoquinone, and (N-isocyanimino)triphenylphosphorane
Ramazani, Ali
Nasrabadi, Fatemeh Zeinali
Malekzadeh, Asemeh Mashhadi
Ahmadi, Yavar
MONATSHEFTE FUR CHEMIE, 2011, 142 (06): : 625 - 630
[4] Synthesis of sterically congested 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, N,N-dicyclohexylcarbodiimide and (N-isocyanimino)triphenylphosphorane
Nasrabadi, Fatemeh Zeinali
Ramazani, Ali
Ahmadi, Yavar
MOLECULAR DIVERSITY, 2011, 15 (03) : 791 - 798
[5] Synthesis of sterically congested 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, N,N-dicyclohexylcarbodiimide and (N-isocyanimino)triphenylphosphorane
Fatemeh Zeinali Nasrabadi
Ali Ramazani
Yavar Ahmadi
Molecular Diversity, 2011, 15 : 791 - 798
[6] The reaction of (N-isocyanimino)triphenylphosphorane with benzoic acid derivatives:: a novel synthesis of 2-aryl-1,3,4-oxadiazole derivatives
Souldozi, Ali
Ramazani, All
TETRAHEDRON LETTERS, 2007, 48 (09) : 1549 - 1551
[7] Four-Component Preparation of Disubstituted 1,3,4-Oxadiazoles from (N-isocyanimino)triphenylphosphorane, Phenylacetylenecarboxylic Acid, Biacetyl and Primary Amines
Ramazani, Ali
Abdian, Behnaz
Nasrabadi, Fatemeh Zeinali
Shajari, Nahid
Ranjdoost, Zahra
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (11): : 3701 - 3705
[8] One-Pot Efficient Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, Carboxylic Acids, and Aromatic Bis-Aldehydes
Ramazani, Ali
Ahmadi, Yavar
Mahyari, Amir
SYNTHETIC COMMUNICATIONS, 2011, 41 (15) : 2273 - 2282
[9] 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
Ramazani, Ali
Ahmadi, Yavar
Rouhani, Morteza
Shajari, Nahid
Souldozi, Ali
HETEROATOM CHEMISTRY, 2010, 21 (06) : 368 - 372
[10] Efficient One-Pot Synthesis of Disubstituted 1,3.4-Oxadiazole Derivatives from the Reaction of (N-Isocyanimino)triphenylphosphorane, Acetaldehyde, a Secondary Amine, and an Electron-Poor (E)-Cinnamic Acid
Ramazani, Ali
Ahmadi, Yavar
Tarasi, Roghayeh
HETEROATOM CHEMISTRY, 2011, 22 (01) : 79 - 84

← 1 2 3 4 5 →