A novel synthesis of 3-((benzo[d]thiazol-2-ylamino)(phenyl)methyl)-4-hydroxy-1-methylquinolin-2(1H)-one via consecutive C-C and C-N bond formation in water

被引：4

作者：

Yadav, Maruti B. ^{[1
]}

Vagh, Sandip S. ^{[2
]}

Jeong, Yeon Tae ^{[1
]}

机构：

[1] Pukyong Natl Univ, Dept Image Sci & Engn, Busan 608737, South Korea

[2] CSIR Natl Chem Lab, Organ Chem Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2020年 / 46卷 / 08期

关键词：

Green solvent; Quinolines; Thiazole; 4-Hydroxy-1-methylquinolin-2(1H)-one; Multicomponent reactions (MCRs); GREEN SYNTHESIS; DOMINO REACTION; SOLVENT; DERIVATIVES; CATALYST; CONSTRUCTION; ANTICANCER; FORMALDEHYDE; INHIBITORS; DISCOVERY;

D O I：

10.1007/s11164-020-04173-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple, efficient, and eco-friendly protocol has been developed for the synthesis of novel 3-((benzo[d]thiazol-2-ylamino)(4-methoxyphenyl)methyl)-4-hydroxy-1-methylquinolin-2(1H)-one derivatives using a one-pot C-C and C-N bond forming strategy from the reaction of 4-hydroxy-1-methylquinolin-2(1H)-one, 2-aminobenzothiazole and aromatic aldehydes in aqueous solvent without using any metal catalyst. Several advantages of this protocol include its operational simplicity, short reaction time, mild reaction condition, efficient utilization of all the reactants, wide functional group tolerance, using water as an environmentally friendly solvent and non-chromatographic purification procedure. [GRAPHICS] .

引用

页码：3801 / 3815

页数：15

共 53 条

[1]

Afzal O, 2014, EUR J MED CHEM, V07, P44

[2] Design, synthesis and in vitro antimicrobial evaluation of novel Imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole motifs [J].

Al-Tel, Taleb H. ;

Al-Qawasmeh, Raed A. ;

Zaarour, Rania .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (05) :1874-1881

[3] Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents [J].

Alagarsamy, V. ;

Solomon, V. Raja ;

Dhanabal, K. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (01) :235-241

[4] p-toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates [J].

Anuradha, V. ;

Srinivas, P. V. ;

Aparna, P. ;

Rao, J. Madhusudana .

TETRAHEDRON LETTERS, 2006, 47 (28) :4933-4935

[5]

Azam F, 2010, MED CHEM, V25, P826

[6] Green synthesis and characterization of supported gold nanoparticles (Au@PS) from Schisandra chinensis fruit extract: An efficient and reusable catalyst for the synthesis of chromeno[2,3-d]pyrimidin-2-yl)phenol derivatives under solvent-free conditions [J].

Balwe, Sandip Gangadhar ;

Rokade, Ashish A. ;

Park, Seong Soo ;

Jeong, Yeon Tae .

CATALYSIS COMMUNICATIONS, 2019, 128

[7] One-step construction of complex polyheterocycles via a sequential post-GBB cyclization/spiro ring expansion triggered by a [1,5]-hydride shift [J].

Balwe, Sandip Gangadhar ;

Jeong, Yeon Tae .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10) :1628-1632

[8] Green synthesis and characterization of silver nanoparticles (Ag NPs) from extract of plant Radix Puerariae: An efficient and recyclable catalyst for the construction of pyrimido [1,2-b] indazole derivatives under solvent-free conditions [J].

Balwe, Sandip Gangadhar ;

Shinde, Vijay Vilas ;

Rokade, Ashish A. ;

Park, Seong Soo ;

Jeong, Yeon Tae .

CATALYSIS COMMUNICATIONS, 2017, 99 :121-126

[9] A pot-economical and green synthesis of novel (benzo[d]imidazo[2,1-b]thiazol-3-y1)-2H-chromen-2-one in ethanol PEG-600 under catalyst-free conditions [J].

Balwe, Sandip Gangadhar ;

Lim, Kwon Taek ;

Cho, Byung Gwon ;

Jeong, Yeon Tae .

TETRAHEDRON, 2017, 73 (25) :3564-3570

[10] Iron-catalyzed unprecedented formation of benzo[d]imidazo[2,1-b]thiazoles under solvent-free conditions [J].

Balwe, Sandip Gangadhar ;

Jeong, Yeon Tae .

RSC ADVANCES, 2016, 6 (109) :107225-107232

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