An Easy and Efficient Method for the Synthesis of Quinoxalines Using Recyclable and Heterogeneous Nanomagnetic-Supported Acid Catalyst under Solvent-Free Condition

被引:28
作者
Harsha, Kachigere B. [1 ]
Rangappa, Shobith [3 ]
Preetham, Habbanakuppe D. [2 ]
Swaroop, Toreshettahally R. [4 ]
Gilandoust, Maryam [2 ]
Rakesh, Kodgahally S. [2 ]
Rangappa, Kanchugarakoppal S. [2 ]
机构
[1] Sarada Vilas Post Grad Ctr, Dept Chem, Mysuru 570004, Karnataka, India
[2] Univ Mysore, DOS Chem, Mysuru 570006, Karnataka, India
[3] Adichunchangiri Inst Mol Med, Nagamangala 571448, Karnataka, India
[4] Univ Mysore, DOS Organ Chem, Mysuru 570006, Karnataka, India
关键词
alpha-bromoketones; nano-Y-Fe2O3-SO3H; o-PDs; Quinoxalines; C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; SULFONIC-ACID; DIASTEREOSELECTIVE SYNTHESIS; MICROWAVE IRRADIATION; O-PHENYLENEDIAMINES; POWERFUL CATALYST; MOLECULAR-IODINE; ROOM-TEMPERATURE; DERIVATIVES;
D O I
10.1002/slct.201800053
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of quinoxalines from o-phenylenediamines (o-PDs) with electronically diversified 1,2-diketones and alpha-bromoketones via simple cyclocondensation reaction using an heterogeneous nano-Y-Fe2O3-SO3H catalyst has been reported under solvent free condition. Low cost, easy workup, high yield, operational simplicity, less reaction time, environmentally benign nature and catalyst is magnetically retrievable and can be reused up to five catalytic cycles without significant loss in the product yields are the noteworthy features of this protocol.
引用
收藏
页码:5228 / 5232
页数:5
相关论文
共 53 条
[1]   Microwave-assisted, solvent free preparation of 1,5-benzodiazepine derivatives using nanomagnetic-supported sulfonic acid as a recyclable and heterogeneous catalyst [J].
Amoozadeh, Ali ;
Malmir, Masoumeh ;
Koukabi, Nadia ;
Otokesh, Somayeh .
JOURNAL OF CHEMICAL RESEARCH, 2015, (12) :694-697
[2]   Nanomagnetic-supported Sulfonic Acid: Simple and Rapid Method for the Synthesis of ,-Bis-(substituted-benzylidene) Cycloalkanones [J].
Amoozadeh, Ali ;
Kolvari, Eskandar ;
Koukabi, Nadiya ;
Otokesh, Somayeh .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2015, 62 (06) :501-505
[3]   Efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using glycerol as green solvent [J].
Bachhav, Harshal M. ;
Bhagat, Saket B. ;
Telvekar, Vikas N. .
TETRAHEDRON LETTERS, 2011, 52 (43) :5697-5701
[4]   Screening of quinoline, 1,3-benzoxazine, and 1,3-oxazine-based small molecules against isolated methionyl-tRNA synthetase and A549 and HCT116 cancer cells including an in silico binding mode analysis [J].
Bharathkumar, Hanumantharayappa ;
Mohan, Chakrabhavi Dhananjaya ;
Rangappa, Shobith ;
Kang, Taehee ;
Keerthy, H. K. ;
Fuchs, Julian E. ;
Kwon, Nam Hoon ;
Bender, Andreas ;
Kim, Sunghoon ;
Basappa ;
Rangappa, Kanchugarakoppal S. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (36) :9381-9387
[5]   An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst [J].
Bhosale, RS ;
Sarda, SR ;
Ardhapure, SS ;
Jadhav, WN ;
Bhusare, SR ;
Pawar, RP .
TETRAHEDRON LETTERS, 2005, 46 (42) :7183-7186
[6]   Gallium(III) triflate-catalyzed synthesis of quinoxaline derivatives [J].
Cai, Jing-Jing ;
Zou, Jian-Ping ;
Pan, Xiang-Qiang ;
Zhang, Wei .
TETRAHEDRON LETTERS, 2008, 49 (52) :7386-7390
[7]   A new ruthenium-catalyzed approach for quinoxalines from o-phenylenediamines and vicinal-diols [J].
Cho, Chan Sik ;
Oh, Sung Gi .
TETRAHEDRON LETTERS, 2006, 47 (32) :5633-5636
[8]   Laterally-extended porphyrin systems incorporating a switchable unit [J].
Crossley, MJ ;
Johnston, LA .
CHEMICAL COMMUNICATIONS, 2002, (10) :1122-1123
[9]  
Dailey S, 2001, J MATER CHEM, V11, P2238, DOI 10.1039/b104674h
[10]   Cu doped CdS nanoparticles: A versatile and recoverable catalyst for chemoselective synthesis of indolo[2,3-b]quinoxaline derivatives under microwave irradiation [J].
Dandia, Anshu ;
Parewa, Vijay ;
Maheshwari, Shuchi ;
Rathore, Kuldeep S. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 394 :244-252