A facile route for the preparation of disubstituted 1,3,4-oxadiazoles from furfural, carboxylic acids, and secondary amines in the presence of N-isocyaniminotriphenylphosphorane

被引：0

作者：

Ramazani, Ali ^{[1
]}

Fattahi, Nadia ^{[1
]}

Rezaei, Aram ^{[1
]}

Nasrabadi, Fatemeh Zeinali ^{[1
]}

机构：

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

来源：

CHEMIJA | 2012年 / 23卷 / 03期

关键词：

N-isocyaniminotriphenylphosphorane; furfural; carboxylic acid; 1,3,4-oxadiazole; aza-Wittig reaction; secondary amine; ONE-POT; 4-COMPONENT SYNTHESIS; MULTICOMPONENT REACTIONS; 3-COMPONENT REACTION; (E)-CINNAMIC ACIDS; DERIVATIVES; (N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE; ISOCYANIDE;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple method has been developed for four-component synthesis of disubstituted 1,3,4-oxadiazoles using N-isocyaniminotriphenylphosphorane, a secondary amine, carboxylic acid, and furfural in CH2Cl2 by a Ugi-4CR/aza-Wittig sequence at room temperature in fairly high yields without using any catalyst or activation. The procedure provides an alternative method to the preparation of fully substituted 1,3,4-oxadiazoles.

引用

页码：255 / 261

页数：7

共 50 条

[1] FOUR-COMPONENT SYNTHESIS OF DISUBSTITUTED 1,3,4-OXADIAZOLES FROM N-ISOCYANIMINOTRIPHENYLPHOSPHORANE, PHENYLACETYLENECARBOXYLIC ACID, CHLOROACETONE DERIVATIVES, AND PRIMARY AMINES
Ramazani, Ali
Nasrabadi, Fatemeh Zeinali
Karimi, Zahra
Rouhani, Morteza
SYNTHETIC COMMUNICATIONS, 2013, 43 (13) : 1818 - 1830
[2] N-ISOCYANIMINOTRIPHENYLPHOSPHORANE AS AN EFFICIENT REAGENT FOR THE SYNTHESIS OF DISUBSTITUTED 1,3,4-OXADIAZOLES VIA IN-SITU GENERATION OF STERICALLY CONGESTED IMINOPHOSPHORANE DERIVATIVES
Ramazani, Ali
Ashtari, Mona
Souldozi, Ali
Ahmadi, Yavar
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (09) : 1064 - 1073
[3] PREPARATION OF 2-DISUBSTITUTED AND 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES FROM TETRAZOLES AND CARBOXYLIC-ACIDS
POVAZANEC, F
KOVAC, J
SVOBODA, J
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1980, 45 (04) : 1299 - 1300
[4] 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
[5] Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines
Ramazani, Ali
Nasrabadi, Fatemeh Zeinali
Karimi, Zahra
Rouhani, Morteza
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (08) : 2700 - 2704
[6] 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
[7] Reaction between N-Isocyaniminotriphenylphosphorane, Aldehydes, and Carboxylic Acids: A One-Pot and Three-Component Synthesis of 2-Aryl-5-hydroxyalkyl-1,3,4-oxadiazoles
Adib, Mehdi
Kesheh, Mahdi Riazati
Ansari, Samira
Bijanzadeh, Hamid Reza
SYNLETT, 2009, (10) : 1575 - 1578
[8] 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
[9] Four-component synthesis of ferrocene-containing 1,3,4-oxadiazoles from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a cyclic ketone and ferrocene carboxylic acid
Ashtary, Mona
Ramazani, Ali
Kazemizadeh, AliReza
Shajari, Nahid
Fattahi, Nadia
Joo, Sang Woo
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (10) : 1402 - 1407
[10] Four-component synthesis of 1,3,4-oxiadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic carboxylic acids, aromatic bis-aldehydes, and secondary
Ramazani, Ali
Karimi, Zahra
Souldozi, Ali
Ahmadi, Yavar
TURKISH JOURNAL OF CHEMISTRY, 2012, 36 (01) : 81 - 91

← 1 2 3 4 5 →