A Catalyst-Free Domino Protocol for the Chemoselective Synthesis of Multifunctionalised Pyrroles in Aqueous Media via Nitroketene-N,S-Acetal Chemistry

被引：11

作者：

Chaudhary, Ankita ^{[1
]}

Khurana, Jitender M. ^{[2
]}

Khanna, Garima ^{[2
]}

Saroha, Mohit ^{[2
]}

机构：

[1] Univ Delhi, Maitreyi Coll, Dept Chem, Bapu Dham Complex, New Delhi 110021, India

[2] Univ Delhi, Dept Chem, New Delhi 110007, India

来源：

CHEMISTRYSELECT | 2018年 / 3卷 / 23期

关键词：

Chemoselective Protocol; Green Chemistry; Group-assisted Purification; (E)-N-Methyl-1-(methylthio)-2-nitroethenamine; Pyrroles; MULTICOMPONENT REACTIONS; GREEN CHEMISTRY; PHARMACEUTICAL-INDUSTRY; CHEMICAL-PROCESSES; HETEROCYCLES; EFFICIENT; DERIVATIVES; METRICS; ACID; INHIBITOR;

D O I：

10.1002/slct.201800831

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of novel 5-(1-methyl-5-(methylthio)-4-nitro-2-aryl-1H-pyrrol-3-yl)pyrimidine-triones was chemoselectively synthesized in excellent yields via catalyst-free three component domino reactions of arylglyoxal monohydrate, (E)-N-methyl-1-(methylthio)-2-nitroethenamine and 1,3-dimethyl barbituric acid/ barbituric acid in aqueous media. The prominent features of the established protocol are its environmentally benign nature, avoidance of catalyst, ease of execution, column free separation, short reaction time, excellent yield of product, high atom economy and low E-factor.

引用

页码：6334 / 6337

页数：4

共 50 条

[1]

Almerico A. M., 2000, ARKIVOC, V2000, P4

[2]

Anastas P. T., 1998, GREEN CHEM FRONTIERS, P166

[3]

Andraos, 2005, J ORG PROCESS RES DE, V9, P149

[4] Synthesis of some newer derivatives of substituted quinazolinonyl-2-oxo/thiobarbituric acid as potent anticonvulsant agents [J].

Archana ;

Srivastava, VK ;

Kumar, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (05) :1257-1264

[5] A new rationale of reaction metrics for green chemistry.: Mathematical expression of the environmental impact factor of chemical processes [J].

Auge, Jacques .

GREEN CHEMISTRY, 2008, 10 (02) :225-231

[6] Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics [J].

Bhardwaj, Varun ;

Gumber, Divya ;

Abbot, Vikrant ;

Dhiman, Saurabh ;

Sharma, Poonam .

RSC ADVANCES, 2015, 5 (20) :15233-15266

[7] Recent advances in multicomponent reactions for diversity-oriented synthesis [J].

Biggs-Houck, James E. ;

Younai, Ashkaan ;

Shaw, Jared T. .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (03) :371-382

[8] Novel bromopyrrole alkaloids from the sponge Agelas dispar [J].

Cafieri, F ;

Fattorusso, E ;

Taglialatela-Scafati, O .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (01) :122-125

[9] Aroyl(aminoacyl)pyrroles, a new class of anticonvulsant agents [J].

Carson, JR ;

Carmosin, RJ ;

Pitis, PM ;

Vaught, JL ;

Almond, HR ;

Stables, JP ;

Wolf, HH ;

Swinyard, EA ;

White, HS .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (11) :1578-1584

[10]

Chao J.L., 2005, CHEM REV, V105, P3095

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