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
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
    Bhattacharya, Asish K.
    Rana, Kalpeshkumar C.
    Mujahid, Mohammad
    Sehar, Irum
    Saxena, Ajit K.
    [J]. 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
    Bigdeli, Mohammad A.
    Heravi, Majid M.
    Mahdavinia, Gholam Hossein
    [J]. 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
    Bigdeli, Mohammadali
    [J]. 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
    Dabiri, Minoo
    Baghbanzadeh, Mostafa
    Nikcheh, Maryam Shakouri
    Arzroomchilar, Elham
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (01) : 436 - 438
  • [6] An efficient synthesis of 1,8-dioxo-octahydroxanthenes using heterogeneous catalysts
    Das, Biswanath
    Thirupathi, Ponnaboina
    Reddy, K. Ravinder
    Ravikanth, B.
    Nagarapu, Lingaiah
    [J]. 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
    Hasaninejad, Alireza
    Zare, Abdolkarim
    Shekouhy, Mohsen
    Ameri-Rad, Javad
    [J]. 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
    Hasaninejad, Alireza
    Zare, Abdolkarim
    Shekouhy, Mohsen
    [J]. 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
    Hasaninejad, Alireza
    Zare, Abdolkarim
    Shekouhy, Mohsen
    Rad, Javad Ameri
    [J]. 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
    Hasaninejad, Alireza
    Zare, Abdolkarim
    Mohammadizadeh, Mohammad Reza
    Shekouhy, Mohsen
    Moosavi-Zare, Ahmad Reza
    [J]. E-JOURNAL OF CHEMISTRY, 2010, 7 (04) : 1546 - 1554