Conversion of β-Nitrostyrenes to Naphthofurans via a Cascade Reaction with α- and β-Naphthols

被引：10

作者：

Abtahi, Bahareh ^{[1
]}

Tavakol, Hossein ^{[1
]}

机构：

[1] Isfahan Univ Technol, Dept Chem, Esfahan 8415683111, Iran

来源：

CHEMISTRYSELECT | 2020年 / 5卷 / 40期

关键词：

Choline chloride; Green chemistry; Heterocycles; Naphthofuran; Naphthol; Nitrostyrene; DEEP EUTECTIC SOLVENT; CHOLINE CHLORIDE; DERIVATIVES; EFFICIENT; ACID; REARRANGEMENT; CATALYST; DESS;

D O I：

10.1002/slct.202003442

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A safe and straightforward method has been developed for the synthesis of various naphthofurans derivatives from readily available alpha,beta-unsaturated nitroalkenes and naphthols in ChCl/ZnCl2 DES media via a cascade reaction. The employed methodology is solvent-free, and ChCl/ZnCl2 DES is applied with the reaction media and catalyst dual roles. Via this reaction, 13 different naphthofuran derivatives, starting from both alpha- ad beta-naphthols have been prepared at 60 degrees C in 4 h with 86-94 % yields.

引用

页码：12582 / 12585

页数：4

共 35 条

[1] Synthesis of 3-aryl-benzo[b]furans and 3-aryl-naphtho[b]furans using n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride immobilised on SiO2 as an efficient and reusable catalyst [J].

Abarghooei, Mohammad Akrami ;

Mohebat, Razieh ;

Karimi-Jaberi, Zahed ;

Mosslemin, Mohammad Hossein .

JOURNAL OF CHEMICAL RESEARCH, 2018, (02) :86-89

[2] Novel solvent properties of choline chloride/urea mixtures [J].

Abbott, AP ;

Capper, G ;

Davies, DL ;

Rasheed, RK ;

Tambyrajah, V .

CHEMICAL COMMUNICATIONS, 2003, (01) :70-71

[3] SYNTHESIS OF BENZOFURAN DERIVATIVES VIA DIFFERENT METHODS [J].

Abu-Hashem, Ameen A. ;

Hussein, Hoda A. R. ;

Aly, Ahmed S. ;

Gouda, Moustafa A. .

SYNTHETIC COMMUNICATIONS, 2014, 44 (16) :2285-2312

[4] Deep Eutectic Solvents: The Organic Reaction Medium of the Century [J].

Alonso, Diego A. ;

Baeza, Alejandro ;

Chinchilla, Rafael ;

Guillena, Gabriela ;

Pastor, Isidro M. ;

Ramon, Diego J. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (04) :612-632

[5] Multicomponent domino reactions in deep eutectic solvent: An efficient strategy to synthesize multisubstituted cyclohexa-1,3-dienamines [J].

Azizi, Najmedin ;

Ahooie, Tahereh Soleymani ;

Hashemi, Mohammad Mahmoudi .

JOURNAL OF MOLECULAR LIQUIDS, 2017, 246 :221-224

[6] Eco-efficiency and scalable synthesis of bisamides in deep eutectic solvent [J].

Azizi, Najmedin ;

Alipour, Masoumeh .

JOURNAL OF MOLECULAR LIQUIDS, 2015, 206 :268-271

[7] Enantioselective Synthesis of Atropisomers with Multiple Stereogenic Axes [J].

Bao, Xiaoze ;

Rodriguez, Jean ;

Bonne, Damien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (31) :12623-12634

[8] ACID-CATALYZED REARRANGEMENT OF CYCLOBUTANONES .5. PREPARATION OF POLYCYCLIC AROMATIC DIHYDROFURANS AND DIHYDROPYRANS [J].

DUPERROUZEL, P ;

LEERUFF, E .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (01) :51-54

[9] Total synthesis of natural products containing benzofuran rings [J].

Heravi, Majid M. ;

Zadsirjan, Vahideh ;

Hamidi, Hoda ;

Amiri, Parvin Hajiabbas Tabar .

RSC ADVANCES, 2017, 7 (39) :24470-24521

[10] Ruthenium-Catalyzed Enantioselective [3+3] Cycloaddition of Propargylic Alcohols with 2-Naphthols [J].

Kanao, Keiichiro ;

Miyake, Yoshihiro ;

Nishibayashi, Yoshiaki .

ORGANOMETALLICS, 2010, 29 (09) :2126-2131

← 1 2 3 4 →