Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c ]coumarins

被引:12
作者
Olyaei, Abolfazl [1 ]
Saraei, Mahnaz [1 ]
Khoeiniha, Reyhaneh [1 ]
机构
[1] Payame Noor Univ, Dept Chem, POB 19395-4697, Tehran, Iran
关键词
furo[3,2-c ]coumarin; phenylglyoxal monohydrate; 4-hydroxycoumarin; heteroarylamine; multicomponent reaction; SOLVENT-FREE CONDITIONS; EFFICIENT; FUROCOUMARINS; COUMARINS; CASCADE; WATER; HETEROCYCLES; CYCLIZATION; ANNULATION; RELEASE;
D O I
10.1055/s-0036-1591582
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c ]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.
引用
收藏
页码:1589 / 1592
页数:4
相关论文
共 33 条
[1]   AN EFFICIENT ONE POT SYNTHESIS OF 2,3-DIPHENYL-4(H)OXOFURO(3,2-C)(1)BENZOPYRANS [J].
AHLUWALIA, VK ;
ADHIKARI, R ;
SINGH, RP .
SYNTHETIC COMMUNICATIONS, 1985, 15 (13) :1191-1196
[2]  
[Anonymous], NATURAL COUMARINS
[3]   One-pot synthesis of furocoumarins via sequential Pd/Cu-catalyzed alkynylation and intramolecular hydroalkoxylation [J].
Chen, Lei ;
Li, Yi ;
Xu, Ming-Hua .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) :3073-3077
[4]   Two efficient cascade reactions to synthesize substituted furocoumarins [J].
Cheng, Gang ;
Hu, Youhong .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4732-4735
[5]   One-pot synthesis of furocoumarins through cascade addition-cyclization-oxidation [J].
Cheng, Gang ;
Hu, Youhong .
CHEMICAL COMMUNICATIONS, 2007, (31) :3285-3287
[6]   Et3N-Induced Demethylation-Annulation of 3-Alkynyl-4-methoxy-2-pyridones and Structurally Related Compounds in the Synthesis of Furan-Fused Heterocycles [J].
Conreaux, David ;
Belot, Sebastien ;
Desbordes, Philippe ;
Monteiro, Nuno ;
Balme, Genevieve .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8619-8622
[7]   Microwave assisted synthesis and biological activity of 3-aryl-furo[3,2-c]coumarins [J].
Kaneria, Ankit R. ;
Giri, Rakesh R. ;
Bhila, Varun G. ;
Prajapati, Hemali J. ;
Brahmbhatt, Dinkar I. .
ARABIAN JOURNAL OF CHEMISTRY, 2017, 10 :S1100-S1104
[8]   Anti-inflammatory effect of coumarins isolated from Corydalis heterocarpa in HT-29 human colon carcinoma cells [J].
Kang, Kyong-Hwa ;
Kong, Chang-Suk ;
Seo, Youngwan ;
Kim, Moon-Moo ;
Kim, Se-Kwon .
FOOD AND CHEMICAL TOXICOLOGY, 2009, 47 (08) :2129-2134
[9]   Catalyst-free synthesis of novel 4H-indeno[1,2-b] furan-4-ones and furo[2,3-d]pyrimidines in water [J].
Khoeiniha, Reyhaneh ;
Olyaei, Abolfazl ;
Saraei, Mahnaz .
SYNTHETIC COMMUNICATIONS, 2018, 48 (02) :155-160
[10]   Water-Based Synthesis of Novel 6, 7-Dihydrobenzofuran-4 (5H) -Ones [J].
Khoeiniha, Reyhaneh ;
Olyaei, Abolfazl ;
Saraei, Mahnaz .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (03) :1746-1750