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

[21] The GAP chemistry for chiral N-phosphonyl imine-based Strecker reaction [J].

Kaur, Parminder ;

Wever, Walter ;

Pindi, Suresh ;

Milles, Raizada ;

Gu, Peng ;

Shi, Min ;

Li, Guigen .

GREEN CHEMISTRY, 2011, 13 (05) :1288-1292

[22] Asymmetric catalytic Strecker reaction of N-phosphonyl imines with Et2AlCN using amino alcohols and BINOLs as catalysts [J].

Kaur, Parminder ;

Pindi, Suresh ;

Wever, Walter ;

Rajale, Trideep ;

Li, Guigen .

CHEMICAL COMMUNICATIONS, 2010, 46 (24) :4330-4332

[23] An expedient four-component domino protocol for the synthesis of novel benzo[a]phenazine annulated heterocycles and their photophysical studies [J].

Khurana, Jitender M. ;

Chaudhary, Ankita ;

Lumb, Anshika ;

Nand, Bhaskara .

GREEN CHEMISTRY, 2012, 14 (08) :2321-2327

[24] Aqua mediated indium(III) chloride catalyzed synthesis of fused pyrimidines and pyrazoles [J].

Khurana, Jitender M. ;

Chaudhary, Ankita ;

Nand, Bhaskara ;

Lumb, Anshika .

TETRAHEDRON LETTERS, 2012, 53 (24) :3018-3022

[25] Catalytic Organic Reactions in Water toward Sustainable Society [J].

Kitanosono, Taku ;

Masuda, Koichiro ;

Xu, Pengyu ;

Kobayashi, Shu .

CHEMICAL REVIEWS, 2018, 118 (02) :679-746

[26] A novel class of highly potent, selective, and non-peptidic inhibitor of Ras farnesyltransferase (FTase) [J].

Lee, H ;

Lee, J ;

Lee, S ;

Shin, Y ;

Jung, WH ;

Kim, JH ;

Park, K ;

Kim, K ;

Cho, HS ;

Ro, S ;

Lee, S ;

Jeong, S ;

Choi, T ;

Chung, HH ;

Koh, JS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (23) :3069-3072

[27]

Li C.-J., 2007, ORGANIC REACTIONS AQ, V2nd

[28] Anti-invasive, antitumoral, and antiangiogenic efficacy of a pyrimidine-2,4,6-trione derivative, an orally active and selective matrix metalloproteinases inhibitor [J].

Maquoi, E ;

Sounni, NE ;

Devy, L ;

Olivier, F ;

Frankenne, F ;

Krell, HW ;

Grams, F ;

Foidart, JM ;

Noël, A .

CLINICAL CANCER RESEARCH, 2004, 10 (12) :4038-4047

[29]

Metzner P., 1994, SULFUR REAGENTS ORGA

[30] An efficient and eco-friendly synthesis of 2-pyridones and functionalized azaxanthone frameworks via indium triflate catalyzed domino reaction [J].

Poomathi, N. ;

Perumal, P. T. ;

Ramakrishna, S. .

GREEN CHEMISTRY, 2017, 19 (11) :2524-2529

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