One Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Polystyrene-supported Ferric Chloride

doi:10.3724/SP.J.1095.2014.30401

Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles Next Articles

One Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Polystyrene-supported Ferric Chloride

XIAO Liwei^*, KONG jie, ZHOU Qiuxiang, HU Yueli

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

Received:2013-08-04 Revised:2013-11-01 Published:2014-06-10 Online:2014-06-10

Abstract

Abstract: A novel polystyrene-supported ferric chloride catalyst was prepared and characterized by IR, XRD and SEM. The catalyst exhibited excellent catalytic activities for the synthesis of β-amino ketone derivatives via one-pot Mannich reaction from acetophenone, aromatic aldehydes and aromatic amines. The catalyst could be recycled easily and the activity of the catalyst maintained after 4 cycles.

Key words: polystyrene-supported ferric chloride, &, beta, -amino ketone, Mannich reaction, one-pot method

CLC Number:

O621.3

XIAO Liwei*, KONG jie, ZHOU Qiuxiang, HU Yueli. One Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Polystyrene-supported Ferric Chloride[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30401.

References

[1] Ting A,Schaus S E. Organocatalytic Asymmetric Mannich Reactions:New Methodology, Catalyst Design, and Synthetic Applications[J]. Eur J Org Chem,2007:5797-5815.

[2] XU Xiujuan,CHEN Guangxu. Mannich Reaction of Aromatic Amines[J]. Acta Chim Sin,1982，40(5):63-468(in Chinese).

徐秀娟，陈光旭. 芳香胺参加的Mannich反应[J]. 化学学报，1982，40(5)：463-468.

[3] CHEN Guangxu,XU Xiujuan,LIU Lijun. Mannich reaction of Aromatic Amines Synthesis of β-Amino Ketones from Aromatic Amine Hydrochloride[J]. Chem J Chinese Univ,1982，3：83-90(in Chinese).

陈光旭，徐秀娟，刘利军. 芳香胺参加的Mannich反应-用芳胺盐酸盐合成β-氨基酮[J]. 高等学校化学学报，1982，3：83-90.

[4] Manabe K，Kobayashi S. Mannich-type Reactions of Aldehydes, Amines, and Ketones in a Colloidal Dispersion System Created by a Brnsted Acid-surfactant-combined Catalyst in Water[J]. Org Lett，1999,1:1965-1967.

[5] Limura S，Nobutou D，Manabe K,et al. Mannich-type Reactions in Water Using a Hydrophobic Polymer-supported Sulfonic Acid Catalyst[J]. Chem Commun，2003：1644-1645.

[6] Li J Z,Peng Y Q,Song G H. Mannich Reaction Catalyzed by Carboxyl-functionalized Ionic Liquid in Aqueous Media[J]. Catal Lett,2005，102:159-162.

[7] WANG Limin,HAN Jianwei,SHENG Jia,et al. Yb(OTf)3 Catalyzed Mannich Reaction of Acetophenone with Aromatic Aldehydes and Aromatic Amines：Three Component One-pot Synthesis of β-Amino Ketone Derivatives[J]. Chinese J Org Chem,2005，25:591-594(in Chinese).

王利民，韩建伟，盛佳，等. Yb(OTf)3催化苯乙酮、芳香醛和芳香胺的Mannich反应：三组分“一锅法”合成β-氨基酮衍生物[J]. 有机化学，2005，25:591-594.

[8] Wang L M,Han J W,SHENG J. Rare Earth Perfluorooctanoate [RE(PFO)3] Catalyzed One-pot Mannich Reaction:Three Component Synthesis of β-Amino Carbonyl Compounds[J]. Catal Commun，2005，6:201-204.

[9] Aziri N，Torklyan L，Saidi M R.Highly Efficient One-pot Three-component Mannich Reaction in Water Catalyzed by Heleropoly Acids[J]. Org Lett，2006，8(10):2079-2082.

[10] Chang C T，Liao B S，Liu S T. Mannich-type Reactions in a Colloidal Solutionformed by Sodium Tetrakis (3,5-Trifluoromethylphenyl)borate as a Catalyst in Water[J]. Tetrahedron Lett，2006，47:9257-9259.

[11] Wang R，Li B G，Huang T K，et al. NbCI5—Catalyzed One-pot Mannich-type Reaction：Three Component Synthesis of β-Amino Carbonyl Compounds[J]. Tetrahedron Lett，2007，48(12)：2071-2073.

[12] Li Z,Ma X L,Liu J,et al. Silica-supported Alumillum Chloride：A Recyclable and Reusable Catalyst for One-pot Three-component Mannich-type Reactions[J]. J Mol Catal A：Chem，2007，272：132-135.

[13] WANG Min,SONG Zhiguo,TIAN Guifu. Synthesis of Multiaryl-substituted β-Amino Ketone Derivatives Catalysed by Aluminium Chloride[J]. Chem Bull,2009，6:84-844(in Chinese).

王敏，宋志国，田桂馥. 氯化铝催化合成多芳基取代β-氨基酮衍生物[J]. 化学通报，2009，6:841-844.

[14] SONG Zhiguo,LIANG Yan,WANG Min. Synthesis of β-Amino Ketone Derivatives Catalyzed by Aluminium Benzenesulfonate from Acetophenone, Aromatic Aldehydes and Aromatic Amines[J]. Chem Res Appl,2010,22(11):1462-1466(in Chinese).

宋志国，梁艳，王敏. 苯磺酸铝催化苯乙酮、芳香醛和芳香胺合成β-氨基酮衍生物[J]. 化学研究与应用,2010,22(11):1462-1466.

[15] WANG Min,LIANG Yan,SONG Zhiguo,et al. Efficient One-pot Synthesis of Amino Derivatives Catalysted by Aluminium p-Toluenesulfonate under Mild Conditions[J]. Chinese J Org Chem,2010,30(2):295-298(in Chinese).

王敏,梁艳，宋志国，等. 温和条件下对甲基苯磺酸铝高效催化一锅法合成-氨基同衍生物[J]. 有机化学，2010,30(2)：295-298

[16] SONG Yang,TANG Xiaomeng,HOU Xiaomeng,et al. Advances of Iron(Ⅲ) Chloride-catalyzed Organic Reactions[J]. Chinese J Org Chem,201，33：76-89 (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.

[17] ZHENG Changwu,CHAI Zhuo,ZHAO Gang. Polymer-Supported Catalysts Designing， Synthesis and Their Application on Organic Synthetic Reaction[J]. Prog Chem,2010,22(7):1442-1456(in Chinese).

郑昌武,柴卓,赵刚. 高分子负载催化剂的设计、合成及其在有机合成反应中的应用[J]. 化学进展,2010,22(7):1442-1456.

[18] XIAO Liwei,JING Xuemin,KONG Jie. Synthesis and Catalytic Behaviors Toward Styrene Polymerization of Zinc Complexes Bearing 6-Benzimidazolyl-2-aryliminoethyl Pyridine[J]. Chinese J Org Chem,2013,33（8）:1828-1833(in Chinese).

肖立伟，景学敏，孔洁. 6-苯并咪唑基-2-芳亚胺乙基吡啶锌配合物的合成及其对苯乙烯聚合的催化性能[J]. 有机化学，2013，33（8）：1828-1833.

[19] LIU Fuan,LU Yan,HUANG Huamin. Synthesis of Polymer Catalysts and Its Use for Addition and Esterification Reaction[J]. Petrochem Technol,1990,19:814-818(in Chinese).

刘福安，吕燕，黄化民. 高分子载体FeCl3催化剂的合成及在加成酯化反应中的应用[J]. 石油化工，1990,19:814-818.

[20] WU Qin,DONG Binqi,HAN Minghan,et al. Synthesis and Characterization of Novel Bronsted Acidic Ionic Liquids[J]. Spectrosc Spectr Anal,2007,27(3):2027-2031(in Chinese).

吴芹,董斌琦,韩明汉,等. 新型Bronsted酸性离子液体的合成与表征[J]. 光谱学与光谱分析,2007,27(3)：2027-2031.

[21] YANG Yali,WANG Xiaohua,KOU Yuan. Determination of Acidity of Ionic Liquids and Alkylation of Isobutane with Butene by Chloroaluminate Ionic Liquids[J]. Chinese J Catal,2004,25:60-64(in Chinese).

杨雅立,王晓化,寇元. 离子液体的酸性测定及其催化的异丁烷/丁烯烷基化反应[J]. 催化学报，2004,25:60-64.

One Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Polystyrene-supported Ferric Chloride

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	De-Hong YANG, Yang YANG, Kun WANG, Wen-Jie FAN, Fang HE, Liu-Xue ZHANG, Yao-Min ZHAO. Explosives & Propellants and Chemistry [J]. Chinese Journal of Applied Chemistry, 2023, 40(6): 916-922.
[2]	Shi-Shuai LI, Jia-Qi LIU, Jia-Yi WANG, Jiang-Feng YANG. Research Progress on Synthesis of Hierarchical Beta Zeolites [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 912-926.
[3]	ZHANG Huili, LI Ke, HUANG Wenlong, WANG Rui, HU Guoqiang. Synthesis and Antitumor Activity of N-Arylidene-Rhodanine Levofloxacin Amides [J]. Chinese Journal of Applied Chemistry, 2019, 36(8): 897-903.
[4]	WANG Liming,MU Hongwen,LU Dongze,LI Xuetao,LI Tong,JIN Ying. Organocatalyzed Asymmetric Mannich Reaction of Isocyanoacetate with Tosylimines [J]. Chinese Journal of Applied Chemistry, 2019, 36(7): 758-763.
[5]	TANG Yucai, WANG Ping, RAN Shutong, CHEN Piao. Synthesis of (E)-β-Vinyl Sulfones by Metal-Free Tetrabutylammonium Iodide/Potassium Persulfate Mediated Radical Denitrative Sulfonylation of β-Nitrostyrenes with Sulfonylhydrazides [J]. Chinese Journal of Applied Chemistry, 2019, 36(6): 664-670.
[6]	YUAN Ning,DU Bingjie,JIA Xiaoxia,YANG Jiangfeng,LI Jinping. Research Progress in Preparation Technology and Application of Bimetal Metal-Organic Frameworks Materials [J]. Chinese Journal of Applied Chemistry, 2018, 35(5): 500-510.
[7]	YAO Feifei, CUI Wei, XIAO Dehai, ZHANG Jifeng. Synthesis of Amoxicillin Inpurity L [J]. Chinese Journal of Applied Chemistry, 2017, 34(7): 768-773.
[8]	XIE Rongjun,ZHOU Tianliang,TAKAHAHIS Kohei,HIROSAKI Naoto. Beta-Sialon(Si_6-_zAl_zO_zN_8-_z):Eu²⁺:A Promising Narrow-band Green Phosphor for Light-emitting Diode Backlights [J]. Chinese Journal of Applied Chemistry, 2016, 33(8): 855-866.
[9]	ZHOU Yehong, MA Xuewen, LIANG Wenting, DONG Chuan, SHUANG Shaomin. Preparation and Physicochemical Properties of the Inclusion Complexes of β-Carotene with β-Cyclodextrin and Its Derivatives [J]. Chinese Journal of Applied Chemistry, 2016, 33(7): 827-833.
[10]	TIAN Zhenhua, ZHANG Hao, YU Yuanhua. Turbidimetry Assay for Detection of beta-Glucan by Gαa Binding Protein [J]. Chinese Journal of Applied Chemistry, 2016, 33(6): 727-732.
[11]	ZHANG Tianyi, NIAN Wenxia, JIN Ying . Organocatalytic Asymmetric Michael Addition of Anthrone with β-Nitroolefins [J]. Chinese Journal of Applied Chemistry, 2015, 32(4): 422-427.
[12]	LYU Chengwei, LIU Yanhang, WANG Jiajing, ZHOU Xiaoxia. Potassium Dihydrogen Phosphate Catalyzed Yonemitsu Condensation for Synthesis of 5-[(Indol-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane- 4,6-dione Derivatives [J]. Chinese Journal of Applied Chemistry, 2015, 32(12): 1371-1378.
[13]	TANG Xuemei, FAN Li, ZHAO Qin, YANG Dacheng. Synthesis and Bioactivities of β-Amino Ketones Containing Sulfadiazine Moiety [J]. Chinese Journal of Applied Chemistry, 2015, 32(11): 1231-1239.
[14]	LI Yuanyuan, ZHAO Chuande, ZHANG Haixia. Preparation of Molecularly Imprinted Solid Phase Extraction Column Using Double Functional Monomers for the Determination of trans-Resveratrol [J]. Chinese Journal of Applied Chemistry, 2015, 32(11): 1283-1289.
[15]	SUN Linlin, ZHOU Yehong, WANG Fei, SHUANG Shaomin, DONG Chuan. Adsorption Properties of Carboxymethyl-β-cyclodextrin Functionalized Ferroferric Oxide Magnetic Nanocomposites on Rhodamine B [J]. Chinese Journal of Applied Chemistry, 2015, 32(1): 110-117.