Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions

被引：30

作者：

Ghorashi, Nadia ^{[1
]}

Shokri, Zahra ^{[1
]}

Moradi, Reza ^{[1
]}

Abdelrasoul, Amira ^{[2
]}

Rostami, Amin ^{[1
,2
]}

机构：

[1] Univ Kurdistan, Fac Sci, Dept Chem, Sanandaj 6617715175, Iran

[2] Univ Saskatchewan, Dept Chem & Biol Engn, 57 Campus Dr, Saskatoon, SK S7N 5A9, Canada

来源：

RSC ADVANCES | 2020年 / 10卷 / 24期

关键词：

ONE-POT SYNTHESIS; HETEROGENEOUS CATALYST; SELECTIVE OXIDATION; C-H; EFFICIENT; DDQ; DERIVATIVES; ALCOHOLS; GREEN; 2-ARYLBENZOTHIAZOLES;

D O I：

10.1039/c9ra10303a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80-95% yield) and benzothiazoles (65-98% yield) using air or O-2 as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient, simple and practical than other reported methods due to the use of O-2 as an oxidant, laccase as an eco-friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.

引用

页码：14254 / 14261

页数：8

共 53 条

[1] Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles [J].

Bahrami, Kiumars ;

Khodaei, M. Mehdi ;

Naali, Fardin .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6835-6837

[2] TiO2 nanoparticles catalysed synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles using hydrogen peroxide under ambient light [J].

Bahrami, Kiumars ;

Khodaei, Mohammad M. ;

Naali, Fardin .

JOURNAL OF EXPERIMENTAL NANOSCIENCE, 2016, 11 (02) :148-160

[3] Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles [J].

Bahrami, Kiumars ;

Khodaei, Mohammad M. ;

Nejati, Akbar .

GREEN CHEMISTRY, 2010, 12 (07) :1237-1241

[4] Microwave activated synthesis of 2-aryl-qlainazolin-4(3H) ones [J].

Bakavoli, M. ;

Sabzevari, O. ;

Rahimizadeh, M. .

CHINESE CHEMICAL LETTERS, 2007, 18 (12) :1466-1468

[5] Catalytic stereoselective benzylic C-H functionalizations by oxidative C-H activation and organocatalysis [J].

Benfatti, Fides ;

Capdevila, Montse Guiteras ;

Zoli, Luca ;

Benedetto, Elena ;

Cozzi, Pier Giorgio .

CHEMICAL COMMUNICATIONS, 2009, (39) :5919-5921

[6] Oxidation of the erythro and threo forms of the phenolic lignin model compound 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol by laccases and model oxidants [J].

Bohlin, Christina ;

Lundquist, Knut ;

Jonsson, Leif J. .

BIOORGANIC CHEMISTRY, 2009, 37 (05) :143-148

[7]

Buckle D. R., 1995, ENCY REAGENTS ORGANI, V3, P169

[8] Laccases and phenol oxidases in organic synthesis - a review [J].

Burton, SG .

CURRENT ORGANIC CHEMISTRY, 2003, 7 (13) :1317-1331

[9] Two Decades of Laccases: Advancing Sustainability in the Chemical Industry [J].

Cannatelli, Mark D. ;

Ragauskas, Arthur J. .

CHEMICAL RECORD, 2017, 17 (01) :122-140

[10] Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains [J].

Cao, SL ;

Feng, YP ;

Jiang, YY ;

Liu, SY ;

Ding, GY ;

Li, RT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1915-1917

← 1 2 3 4 5 6 →