Solvent-Free Synthesis of 1,8-Dioxo-octahydroxanthenes and 14-Aryl-14H-dibenzo[a,j]xanthenes using Saccharin Sulfonic Acid as an Efficient and Green Catalyst

被引：21
作者：
Zare, Abdolkarim [1 ]
Mokhlesi, Mohammad [2 ]
Hasaninejad, Alireza [3 ]
Hekmat-Zadeh, Tahereh [1 ]
机构：
[1] Payame Noor Univ, Dept Chem, Tehran, Iran
[2] Bu Ali Sina Univ, Fac Chem, Hamadan 6517838683, Iran
[3] Persian Gulf Univ, Fac Sci, Dept Chem, Bushehr 75169, Iran
来源：
E-JOURNAL OF CHEMISTRY | 2012年 / 9卷 / 04期
关键词：
1,8-Dioxo-octahydroxanthene; 14-Aryl-14H-dibenzo[a; j]xanthene; Saccharin sulfonic acid (SaSA); Sulfonic acid-containing catalyst; One-pot multi-component reaction; Solvent-free; SILICA SULFURIC-ACID; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; IMIDAZOLIUM CHLORIDE; CONDENSATION; DERIVATIVES; HCLO4-SIO2; ALDEHYDES; PROTOCOL; SYSTEM;
D O I：
10.1155/2012/596862
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Saccharin sulfonic acid (SaSA) is utilized as a highly efficient, green and inexpensive sulfonic acid-containing catalyst for the following one-pot multi-component organic transformations: (i) the condensation of dimedone (2 eq.) with aromatic aldehydes (1 eq.) leading to 1,8-dioxo-octahydroxanthenes, and (ii) the reaction of 2-naphthol (2 eq.) with arylaldehydes (1 eq.) leading to 14-aryl-14H-dibenzo[a,j]xanthenes. In these protocols, the title compounds are produced in high to excellent yields and in relatively short reaction times under solvent-free conditions.
引用
收藏
页码：1854 / 1863
页数：10
相关论文
共 48 条
[1]  
[Anonymous], 2006, E-J CHEM
[2]   Synthesis and in vitro study of 14-aryl-14H-dibenzo[a.j]xanthenes as cytotoxic agents [J].
Bhattacharya, Asish K. ;
Rana, Kalpeshkumar C. ;
Mujahid, Mohammad ;
Sehar, Irum ;
Saxena, Ajit K. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (19) :5590-5593
[3]   Silica supported perchloric acid (HClO4-SiO2):: A mild, reusable and highly efficient heterogeneous catalyst for the synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes [J].
Bigdeli, Mohammad A. ;
Heravi, Majid M. ;
Mahdavinia, Gholam Hossein .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 275 (1-2) :25-29
[4]   Clean synthesis of 1,8-dioxooctahydroxanthenes promoted by DABCO-bromine in aqueous media [J].
Bigdeli, Mohammadali .
CHINESE CHEMICAL LETTERS, 2010, 21 (10) :1180-1182
[5]   Eco-friendly and efficient one-pot synthesis of alkyl- or aryl-14H-dibenzo[a,j]xanthenes in water [J].
Dabiri, Minoo ;
Baghbanzadeh, Mostafa ;
Nikcheh, Maryam Shakouri ;
Arzroomchilar, Elham .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (01) :436-438
[6]   An efficient synthesis of 1,8-dioxo-octahydroxanthenes using heterogeneous catalysts [J].
Das, Biswanath ;
Thirupathi, Ponnaboina ;
Reddy, K. Ravinder ;
Ravikanth, B. ;
Nagarapu, Lingaiah .
CATALYSIS COMMUNICATIONS, 2007, 8 (03) :535-538
[7]   Sulfuric acid-modified PEG-6000 (PEG-OSO3H): an efficient, bio-degradable and reusable polymeric catalyst for the solvent-free synthesis of poly-substituted quinolines under microwave irradiation [J].
Hasaninejad, Alireza ;
Zare, Abdolkarim ;
Shekouhy, Mohsen ;
Ameri-Rad, Javad .
GREEN CHEMISTRY, 2011, 13 (04) :958-964
[8]   Highly efficient synthesis of triazolo[1,2-a]indazole-triones and novel spiro triazolo[1,2-a]indazole-tetraones under solvent-free conditions [J].
Hasaninejad, Alireza ;
Zare, Abdolkarim ;
Shekouhy, Mohsen .
TETRAHEDRON, 2011, 67 (02) :390-400
[9]   Catalyst-Free One-Pot Four Component Synthesis of Polysubstituted Imidazoles in Neutral Ionic Liquid 1-Butyl-3-methylimidazolium Bromide [J].
Hasaninejad, Alireza ;
Zare, Abdolkarim ;
Shekouhy, Mohsen ;
Rad, Javad Ameri .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (06) :844-849
[10]   A Green Solventless Protocol for the Synthesis of β-Enaminones and β-Enamino Esters Using Silica Sulfuric Acid as a Highly Efficient, Heterogeneous and Reusable Catalyst [J].
Hasaninejad, Alireza ;
Zare, Abdolkarim ;
Mohammadizadeh, Mohammad Reza ;
Shekouhy, Mohsen ;
Moosavi-Zare, Ahmad Reza .
E-JOURNAL OF CHEMISTRY, 2010, 7 (04) :1546-1554
12345