The Reaction of N-Isocyaniminotriphenylphosphorane with 2-Oxopropylbenzoate (or 4-Bromobenzoate) and a Primary Amine in the Presence of (E)-Cinnamic Acid Derivatives: A One-Pot Efficient Four-Component Reaction for the Synthesis of 2-(Arylamino)-2-(5-aryl-1-ethenyl-1,3,4-oxadiazol-2-yl) Propyl Benzoate (or 4-Bromobenzoate) Derivatives

被引：5

作者：

Ramazani, Ali ^{[1
]}

Ahmadi, Yavar ^{[1
]}

Nasrabadi, Fatemeh Zeinali ^{[1
]}

Rouhani, Morteza ^{[2
]}

机构：

[1] Zanjan Univ, Dept Chem, Zanjan, Iran

[2] Islamic Azad Univ, Zanjan Branch, Young Researchers Club, Zanjan, Iran

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2013年 / 50卷 / 06期

关键词：

SUBSTITUTED 1,3,4-OXADIAZOLE DERIVATIVES; STABILIZED PHOSPHORUS YLIDES; AROMATIC CARBOXYLIC-ACIDS; X-RAY-STRUCTURE; STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT REACTIONS; 3-COMPONENT REACTION; (N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE;

D O I：

10.1002/jhet.1563

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of N-isocyaniminotriphenylphosphorane with 2-oxopropylbenzoate (or 2-oxopropyl 4-bromobenzoate) in the presence of (E)-cinnamic acids and primary amines proceed smoothly at room temperature and in neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in high yields. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed.

引用

页码：1294 / 1298

页数：5

共 40 条

[1] A one-pot efficient four-component reaction for the synthesis of 2-(arylamino)-2-(5-aryl-1-ethenyl-1,3,4-oxadiazol-2-yl)propyl benzoate (or 4-bromobenzoate) derivatives
Holagh, Mohsen Valizadeh
Maharramov, Abel Mohammadalioglu
Allakhverdiev, Mirza Aliakbaroglu
Ramazani, Ali
Ahmadi, Yavar
Nasrabadi, Fatemeh Zeinali
Souldozi, Ali
TURKISH JOURNAL OF CHEMISTRY, 2012, 36 (05) : 671 - 681
[2] A One-Pot Efficient Four-Component Reaction for the Synthesis of 2-(Arylamino)-2-(5-aryl-1,3,4-oxadiazol-2-yl)propyl Benzoate (or Acetate) Derivatives
Ramazani, Ali
Ahmadi, Yavar
Malekzadeh, Asemeh Mashhadi
Rezaei, Aram
HETEROATOM CHEMISTRY, 2011, 22 (06) : 692 - 698
[3] The Reaction of N-Isocyaniminotriphenylphosphorane with Ester Derivatives of 2-Oxopropyl Alcohol (2-Oxopropyl 4-Bromobenzoate, 2-Oxopropyl Benzoate, and 2-Oxopropyl Acetate) in the Presence of Aromatic Carboxylic Acids: A One-Pot Efficient Three-Component Reaction for the Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives
Ramazani, Ali
Ahmadi, Yavar
Karimi, Zahra
Rezaei, Aram
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (06) : 1447 - 1451
[4] Efficient one-pot three-component reaction for the synthesis of (5-aryl-1,3,4-oxadiazol-2-yl)(pyridin-2-yl)methanol derivatives
Souldozi, Ali
JOURNAL OF CHEMICAL RESEARCH, 2015, (03) : 177 - 179
[5] One-Pot Four-Component Synthesis of N2-Alkyl-N3-[2-(1,3,4-oxadiazol-2-yl)aryl]benzofuran-2,3-diamines
Adib, Mehdi
Sheikhi, Ehsan
Karimzadeh, Morteza
Bijanzadeh, Hamid Reza
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HELVETICA CHIMICA ACTA, 2012, 95 (05) : 788 - 794
[6] 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
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Kazemizadeh, Ali Reza
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JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2012, 77 (09) : 1175 - 1180
[7] The Reaction of (N-Isocyanimino)triphenylphosphorane with Biacetyl in the Presence of Aromatic Carboxylic Acids: Efficient One-Pot Three-Component Reaction for the Synthesis of 3-(5-Aryl-1,3,4-oxadiazol-2-yl)-3-hydroxybutan-2-one Derivatives
Ramazani, Ali
Rouhani, Morteza
Rezaei, Aram
Shajari, Nahid
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HELVETICA CHIMICA ACTA, 2011, 94 (02) : 282 - 288
[8] 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
[9] Novel, Simple, and Efficient Synthesis of 3-(2-(5-(Benzylideneamino)-3-phenyl-1H-pyrazol-1-yl)thiazol-4-yl)-4-hydroxy-6-methyl-2H-pyran-2-one Derivatives via a One-Pot, Four-Component Condensation Reaction
Bade, Thirupaiah
Vedula, Rajeswar Rao
SYNTHETIC COMMUNICATIONS, 2015, 45 (20) : 2350 - 2354
[10] (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

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