Alum-Catalyzed Synthesis of 3-(1H-Pyrrol-2-yl)-2H-chromen-2-ones: A Water-PEG 400 Binary Solvent Mediated, One-Pot, Three-Component Protocol

被引：16
作者：
Pal, Gargi [1 ]
Paul, Sanjay [1 ]
Das, Asish R. [1 ]
机构：
[1] Univ Calcutta, Dept Chem, Kolkata 700009, India
来源：
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 09期
关键词：
pyrrole derivatives; coumarin; alum; binary solvent; green protocol; POTENTIAL ANTIVIRAL AGENTS; REUSABLE CATALYST; COUMARIN DERIVATIVES; ANTIOXIDANT ACTIVITY; ACYCLIC DERIVATIVES; BIOLOGICAL-ACTIVITY; (ARYLOXYIMINO)ETHYLCOUMARINS; GLYCOSIDOPYRROLES; PYRROLES; ZNO;
D O I：
10.1055/s-0032-1318494
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel, one-pot, three-component condensation reaction of 3-(bromoacetyl)coumarin, acetylacetone, and an amine using the inexpensive, environmentally benign, and mild catalyst alum as an efficient catalyst and the water-PEG 400 binary solvent system gives 3-(1-aryl-4-acetyl-5-methyl-1H-pyrrol-2-yl)-2H-chromen-2-ones, a new heterocyclic scaffold containing both the coumarin and pyrrole nuclei in a single molecule, in good to excellent yields. This methodology offers several advantages: simple procedure, excellent yields, short reaction times, and green aspects such as avoiding toxic catalysts and solvents.
引用
收藏
页码：1191 / 1200
页数：10
相关论文
共 43 条
[21]   CORRELATION OF PLASMA 4,5-BIS(PARA METHOXYPHENYL)-2-PHENYLPYRROLE-3-ACETONITRILE LEVELS WITH BIOLOGICAL-ACTIVITY [J].
KAISER, DG ;
GLENN, EM .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1972, 61 (12) :1908-&
[22]  
Kawai A., 1998, PCT Int. Appl., Patent No. [WO 9802430 A119980122, CAN 128:140613, 9802430]
[23]   Synthesis and in vitro evaluation of antioxidant activity of diverse naphthopyranopyrimidines, diazaanthra[2,3-d][1,3]dioxole-7,9-dione and tetrahydrobenzo[a]xanthen-11-ones [J].
Khurana, Jitender M. ;
Lumb, Anshika ;
Chaudhary, Ankita ;
Nand, Bhaskara .
RSC ADVANCES, 2013, 3 (06) :1844-1854
[24]  
Kimura T., 2000, [No title captured], Patent No. [WO 0001688, 0001688]
[25]  
Knorr L., 1884, CHEM BER-RECL, V17, P1635, DOI [10.1002/cber.18840170220, DOI 10.1002/CBER.18840170220]
[26]  
Kostova Irena, 2005, Current Medicinal Chemistry - Anti-Cancer Agents, V5, P29, DOI 10.2174/1568011053352550
[27]   Synthesis and antioxidant activity of new tetraarylpyrroles [J].
Lehuédé, J ;
Fauconneau, B ;
Barrier, L ;
Ourakow, M ;
Piriou, A ;
Vierfond, JM .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (11) :991-996
[28]   Bioactive natural products derived from the East African flora [J].
Magadula, Joseph J. ;
Erasto, Paul .
NATURAL PRODUCT REPORTS, 2009, 26 (12) :1535-1554
[29]   EXPEDIENT SYNTHESIS OF BIOLOGICALLY POTENT ARYLOXYCOUMARINS AND (ARYLOXYIMINO)ETHYLCOUMARINS VIA COPPER(II)-PROMOTED CHAN-LAM COUPLING REACTION [J].
Medda, Arunima ;
Pal, Gargi ;
Singha, Raghunath ;
Hossain, Tabassum ;
Saha, Achintya ;
Das, Asish R. .
SYNTHETIC COMMUNICATIONS, 2013, 43 (02) :169-181
[30]  
Muchowski J.M., 1992, Adv. Med. Chem, V1, P109, DOI DOI 10.1096/FJ.01-0024LSF
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