Combinatorial Synthesis of Pyrrolo[3,2-f]quinoline and Pyrrolo[3,2-a]acridine Derivatives via a Three-Component Reaction under Catalyst-Free Conditions

被引：35

作者：

Zhou, Yu-Jing ^{[1
]}

Chen, Dong-Sheng ^{[1
]}

Li, Yu-Ling ^{[1
]}

Liu, Yun ^{[1
]}

Wang, Xiang-Shan ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China

来源：

ACS COMBINATORIAL SCIENCE | 2013年 / 15卷 / 09期

基金：

中国国家自然科学基金;

关键词：

pyrrolo[3,2-f]quinoline; pyrrolo[3,2-a]acridine; 1H-indol-5-amine; catalyst-free; synthesis; ONE-POT SYNTHESIS; CRYSTAL-STRUCTURE; EFFICIENT METHOD; CLEAN PROCEDURE; ACRIDINE;

D O I：

10.1021/co400073m

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A combinatorial synthesis of pyrrolo[3,21]quinoline and pyrrolo[3,2-c]acridine derivatives is described as a three-component reaction of aromatic aldehyde, 1H-indol-S-amine, and 1,3-dicarbonyl compounds under catalyst-free conditions. The 1,3-dicarbonyl compounds include S,S-dimethylcyclohexane-1,3-dione, cyclopentane-1,37 dione, and 2H-indene-1,3-dione. It is interesting that the designed reactions gave aromatized or unaromatized products, which depend on the reaction temperature and reactants of 1,3-dicarbonyl compounds.

引用

收藏

页码：498 / 502

页数：5

相关论文

共 39 条

[1] 4-Chloro-3-iodoquinoline as a Synthon in the Development of New Syntheses of 1,2-Disubstituted 1H-Pyrrolo[3,2-c] quinolines [J].

Almeida, Andreia I. S. ;

Silva, Artur M. S. ;

Cavaleiro, Jose A. S. .

SYNLETT, 2011, (20) :2955-2958

[2] Synthesis of pyrrolo[3,2-h]quinolinones with good photochemotherapeutic activity and no DNA damage [J].

Barraja, Paola ;

Caracausi, Libero ;

Diana, Patrizia ;

Carbone, Anna ;

Montalbano, Alessandra ;

Cirrincione, Girolamo ;

Brun, Paola ;

Palu, Giorgio ;

Castagliuolo, Ignazio ;

Dall'Acqua, Francesco ;

Vedaldi, Daniela ;

Salvador, Alessia .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (13) :4830-4843

[3] Acridine and acridone derivatives, anticancer properties and synthetic methods: Where are we now? [J].

Belmont, Philippe ;

Bosson, Johann ;

Godet, Thomas ;

Tiano, Martin .

ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2007, 7 (02) :139-169

[4]

Bonnet A., 2008, PCT Int. Appl., Patent No. [WO 2008009865 A1, 2008009865]

[5] Artesunate reduces chicken chorioallantoic membrane neovascularisation and exhibits antiangiogenic and apoptotic activity on human microvascular dermal endothelial cell [J].

Chen, HH ;

You, LL ;

Li, SB .

CANCER LETTERS, 2004, 211 (02) :163-173

[6] One-Pot Facile Synthesis of Acridine Derivatives under Solvent-Free Condition [J].

Ghorbani-Vaghei, R. ;

Malaekehpoor, S. M. .

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2010, 7 (04) :957-964

[7]

Han G. P., 2002, Korean Kongkae Taeho Kongbo, Patent No. [KR 2002028391 A 20020417, 2002028391]

[8] NH2SO3H AND H6P2W18O62•18H2O-CATALYZED, THREE-COMPONENT, ONE-POT SYNTHESIS OF BENZO[c]ACRIDINE DERIVATIVES [J].

Heravi, Majid M. ;

Alinejhad, Hamideh ;

Derikvand, Fatemeh ;

Oskooie, Hossein A. ;

Baghernejad, Bita ;

Bamoharram, Fatemeh F. .

SYNTHETIC COMMUNICATIONS, 2012, 42 (14) :2033-2039

[9]

Ippolito A., 2004, Medicinal Chemistry Reviews - Online (Discontinued), V1, P267

[10] One-pot Preparation of Fluorinated Polyhydrobenzoacridine-1-one Derivatives under Microwave Irradiation and Solvent-free Conditions [J].

Jin Jianan ;

Zhang Jianmin ;

Li Fengrui ;

Shang Wenli ;

Xin Yong ;

Zhu Shizheng .

CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (07) :1217-1222

← 1 2 3 4 →