Synthesis of Xanthene Derivatives Catalyzed by Modified Active Carbon Supported Ferric Chloride

doi:10.11944/j.issn.1000-0518.2015.03.140228

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (3): 304-309.DOI: 10.11944/j.issn.1000-0518.2015.03.140228

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Synthesis of Xanthene Derivatives Catalyzed by Modified Active Carbon Supported Ferric Chloride

XIAO Liwei^*, GAO Hongjie, REN Lilei, KANG Jian

Faculty of Chemistry and Material Science,Langfang Teachers University,Langfang,Hebei 065000,China

Received:2014-06-30 Accepted:2014-10-07 Published:2015-03-02 Online:2015-03-02
Contact: Liwei XIAO
Supported by:
Supported by the Natural Science Foundation of Hebei Province(No.B2013408014), Key Foundation of Langfang Teachers University(No.LSLZ201402)

Abstract

Abstract:

A novel modified active carbon supported ferric chloride catalyst(MAC-FeCl₃) has been prepared and characterized by IR and ICP-AES. In the presence of MAC-FeCl₃, condensation of aldehydes and β-naphthol was carried out in PEG 200 to afford a series of xanthene derivatives in 79%~93% yields within 60~120 min. The prepared catalyst can be recycled easily and the activity of catalyst maintains stable after used for 4 times. This affords this methodology the advantages on good yields, less pollution and simple work-up.

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Key words: modified active carbon supported ferric chloride, xanthene derivatives, heterogeneous

CLC Number:

XIAO Liwei, GAO Hongjie, REN Lilei, KANG Jian. Synthesis of Xanthene Derivatives Catalyzed by Modified Active Carbon Supported Ferric Chloride[J]. Chinese Journal of Applied Chemistry, 2015, 32(3): 304-309.

References

[1]	El-Brashy A M,Metwally M E,El-Sepai F A. Spectrophotometric Determination of Some Fluoroquinolone Antibacterials by Binary Complex Formation with Xanthene Dyes[J]. Farmaco,2004,59(10):809-817.
[2]	Chibale K,Visser M R,Schalkwyk D V,et al.Exploring the Potential of Xanthene Derivatives as Trypanothione Reductase Inhibitors and Chloroquine Potentiating Agents[J]. Tetrahedron,2003,59(13):2289-2296.
[3]	Bhowmik B,Ganguly B P. Photophysics of Xanthene Dyes in Surfactant Solution[J]. Spectrochim Acta Part A,2005,61(9):1997-2003.
[4]	Rajitha B,Kumar B S,Reddy Y,et al.Sulfamic Acid: A Novel and Efficient Catalyst for the Synthesis of Aryl-14H- dibenzo[a.j]xanthenes under Conventional Heating and Microwave Irradiation[J]. Tetrahedron Lett,2005,46(50):8691-8693.
[5]	Saini A,Kumar S,Sandhu J S. A New LiBr-Catalyzed,Facile and Efficient Method for the Synthesis of 14-Alkyl or Aryl-14H-dibenzo[a,j]xanthenes and Tetrahydrobenzo[b]pyrans Under Solvent-Free Conventional and Microwave Heating[J]. Synlett,2006,(12):1928-1932.
[6]	LIU Di,YU Yang,ZHANG Shaohua,et al.Catalytic Synthesis of 14-Alkyl (aryl)-14H-dibenzo[a,j]xanthenes Compounds by Sodium Hydrogen Sulfate[J]. Chinese J Synth Chem,2007,15(4):516-518(in Chinese). 刘迪,于杨,张少华,等. 硫酸氢钠催化合成14-烷基(芳基)-14H-二苯并[a,j]氧杂蒽类化合物[J]. 合成化学,2007,15(4):516-518.
[7]	Bigdeli N A,Heravi M M,Mahdavinia G H. Silica Supported Perchloric Acid (HClO4-SiO2):A Mild, Reusable and Highly Efficient Heterogeneous Catalyst for the Synthesis of 14-Aryl or Alkyl-14H-dibenzo [a,j] xanthenes[J]. J Mol Catal A:Chem,2007,275(1/2):25-29.
[8]	Shahnaz R,Nasrin S, ,et al. Silica Supported Sodium Hydrogen Sulfate (NaHSO4/SiO2):A Mild and Efficient Reusable Catalyst for the Synthesis of Aryl-14H-dibenzo [a,j]xanthenes under Solvent-free Conditions[J]. Chinese Chem Lett,2008,19(10):1151-1155.
[9]	Mirjalili B B F,Bamoniri A,Akbari A. BF3 SiO2:An Efficient Alternative for the Synthesis of 14-Aryl or Alkyl-14H-dibenzo[a,j]xanthenes[J]. Tetrahedron Lett,2008,49(45):6454-6456.
[10]	Mahdavinia G H,Rostamizadeh S,Amani A M,et al.Ultrasound-promoted Greener Synthesis of Aryl-14H-dibenzo[a,j]xanthenes Catalyzed by NH4H2PO4/SiO2 in Water[J]. Ultrason Sonochem,2009,16:7-10.
[11]	CHU Huiyuan,ZHANG Huifang,YANG Jinhui,et al.Catalytic Synthesis of 14-Alkyl(aryl)-14H-dibenzo[a,j] xanthene Compounds by the H2SO4 Loaded Coal Based Activated Carbon as Solid Acid Catalyst Under Solvent-Free Condition[J]. Chinese J Org Chem,2009,29(10):1637-1639(in Chinese). 楚惠元,张会芳,杨金会,等. 无溶剂条件下煤基活性炭负载硫酸作为固体酸催化合成14-烷基(芳基)-14H-二苯并[a,j]氧杂蒽类化合物[J]. 有机化学,2009,29(10):1637-1639.
[12]	Kumar R,Nandi G C,Verma K V,et al.A Facile Approach for the Synthesis of 14-Aryl-or Alkyl -14H -dibenzo[a,j]xanthenes under Solvent-free Condition[J]. Tetrahedron Lett,2010,51(2):442-445.
[13]	HAN Bo,LIU Feifei,ZHANG Yuqi,et al.Condensation Reactions Between Aldehydes and β-Naphthol Catalyzed by Silicotungstic Acid[J]. Chinese J Org Chem,2012,32:1121-1125(in Chinese). 韩波,刘飞飞,张玉琦,等. Keggin结构型硅钨酸催化β-萘酚与醛的缩合反应[J]. 有机化学,2012,32:1121-1125.
[14]	Mohammadpoor-Baltork I,Moghadam M,Mirkhani V,et al.Highly Efficient and Green Synthesis of 14-Aryl(alkyl)-14H-dibenzo[a,j]xanthene and 1,8-Dioxooctahydroxanthene Derivatives Catalyzed by Reusable Zirconyl Triflate [ZrO(OTf)2] Under Solvent-free Conditions[J]. Chinese Chem Lett,2011,22(1):9-12.
[15]	Jha A,Bea J. Convenient Synthesis of 12H-Benzo[a]xanthenes from 2-Tetralone[J]. Tetrahedron Lett,2004,45(49):8999-9001.
[16]	Wang B,Li P,Zhang Y,Wang L. FeCl3-Catalyzed Condensation of 2-Naphthol and Aldehydes Under Solvent-Free Reaction Conditions:An Efficient and Green Alternative for the Synthesis of 14-Aryl(Alkyl)- 14H-dibenzo[a,j]xanthenes[J]. Chinese J Chem,2010,28:2463-2468
[17]	SONG Yang,TANG Xuesong,HOU Xiaomeng,et al.Advances of Iron(Ⅲ) Chloride-Catalyzed Organic Reactions[J]. Chinese J Org Chem,2013,33:76-89(in Chinese). 宋阳,唐雪松,侯晓萌,等. 三氯化铁催化的有机反应研究进展[J]. 有机化学,2013,33:76-89.
[18]	XIAO Liwei,KONG Jie,ZHOU Qiuxiang,et al.One Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Polystyrene Supported Ferrie Chloride[J]. Chinese J Appl Chem,2014,31(6):715(in Chinese). 肖立伟,孔洁,周秋香,等. 聚苯乙烯负载氯化铁催化一锅法合成β-氨基酮类衍生物[J]. 应用化学,2014,31(6):715-720.
[19]	LU Yadong,WANG Yanhua,Jin Zilin. Catalysts Supported on PEG and Catalytic Reaction Systems of PEG Used as a Reaction Medium[J]. Chinese J Org Chem,2006,26(2):181-188(in Chinese). 鲁亚东,王艳华,金子林. 以聚乙二醇为载体的催化剂及为反应介质的催化反应体系[J]. 有机化学,2006,26(2):181-188.

Synthesis of Xanthene Derivatives Catalyzed by Modified Active Carbon Supported Ferric Chloride

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