La2O3/TFE: An efficient system for room temperature synthesis of Hantzsch polyhydroquinolines

被引:41
作者
Tekale, Sunil U. [1 ]
Pagore, Vijay P. [1 ]
Kauthale, Sushama S. [2 ]
Pawar, Rajendra P. [2 ]
机构
[1] Shri Muktanand Coll, Dept Chem, Gangapur 431109, India
[2] Deogiri Coll, Dept Chem, Aurangabad 431005, Maharashtra, India
关键词
Hantzsch polyhydroquinolines; La2O3; TFE; ONE-POT SYNTHESIS; REUSABLE HETEROGENEOUS CATALYST; HIGHLY EFFICIENT; DERIVATIVES; CONDENSATION; FACILE; 1,4-DIHYDROPYRIDINES; CHEMISTRY; OXIDE;
D O I
10.1016/j.cclet.2014.03.037
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Lanthanum oxide (La2O3) in combination with 2,2,2-trifluoroethanol (TFE) was found to be an efficient system for the one-pot, four-component synthesis of Hantzsch polyhydroquinoline derivatives from aromatic aldehydes, dimedone, ethyl acetoacetate and ammonium acetate at ambient temperature. The catalyst is heterogeneous and reusable, hence can be separated easily and reused. The present method is featured by mild reaction conditions, use of heterogeneous catalyst, non-chromatographic purification, short reaction time and high yields, which make it an attractive route for the synthesis of polyhydroquinolines. (C) 2014 Rajendra P. Pawar. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:1149 / 1152
页数:4
相关论文
共 34 条
[11]   One-pot Wittig reaction for the synthesis of α,β-unsaturated esters using highly basic magnesium/lanthanum mixed oxide [J].
Kantam, M. Lakshmi ;
Kumar, K. B. Shiva ;
Balasubramanyam, V. ;
Venkanna, G. T. ;
Figueras, F. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 321 (1-2) :10-14
[12]   Efficient synthesis of Hantzsch esters and polyhydroquinoline derivatives in aqueous micelles [J].
Kumar, Atul ;
Maurya, Ram Awatar .
SYNLETT, 2008, (06) :883-885
[13]   Chemistry of precious metal oxides relevant to heterogeneous catalysis [J].
Kurzman, Joshua A. ;
Misch, Lauren M. ;
Seshadri, Ram .
DALTON TRANSACTIONS, 2013, 42 (41) :14653-14667
[14]   Microwave assisted synthesis of novel Hantzsch 1,4-dihydropyridines, acridine-1,8-diones and polyhydroquinolines bearing the tetrazolo[1,5-a]quinoline moiety and their antimicrobial activity assess [J].
Ladani, Niraj K. ;
Mungra, Divyesh C. ;
Patel, Manish P. ;
Patel, Ranjan G. .
CHINESE CHEMICAL LETTERS, 2011, 22 (12) :1407-1410
[15]   An efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation using a heterogeneous catalyst under solvent-free conditions [J].
Maheswara, M ;
Siddaiah, V ;
Damu, GLV ;
Rao, CV .
ARKIVOC, 2006, :201-206
[16]   A Microwave-Assisted Diastereoselective Multicomponent Reaction To Access Dibenzo[c,e]azepinones: Synthesis and Biological Evaluation [J].
Mehta, Vaibhav P. ;
Modha, Sachin G. ;
Ruijter, Eelco ;
Van Hecke, Kristof ;
Van Meervelt, Luc ;
Pannecouque, Christophe ;
Balzarini, Jan ;
Orru, Romano V. A. ;
Van der Eyckent, Erik .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2828-2839
[17]   Rapid and Efficient One-Pot Synthesis of 1,4-Dihydropyridine and Polyhydroquinoline Derivatives Through the Hantzsch Four Component Condensation by Zinc Oxide [J].
Moghaddam, F. Matloubi ;
Saeidian, H. ;
Mirjafary, Z. ;
Sadeghi, A. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2009, 6 (02) :317-324
[18]   An efficient and rapid Mn(III) complex catalyzed synthesis of polyhydropyridine derivatives via Hantzsch four component condensation [J].
Mosaddegh, Elaheh ;
Hassankhani, Asadollah .
ARABIAN JOURNAL OF CHEMISTRY, 2012, 5 (03) :315-318
[19]   A New, Efficient and Recyclable Lanthanum(III) Oxide-Catalyzed C-N Cross-Coupling [J].
Murthy, S. Narayana ;
Madhav, B. ;
Reddy, V. Prakash ;
Nageswar, Y. V. D. .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3241-3245
[20]   Magnetic Fe3O4 nanoparticles: Efficient and recoverable nanocatalyst for the synthesis of polyhydroquinolines and Hantzsch 1,4-dihydropyridines under solvent-free conditions [J].
Nasr-Esfahani, Masoud ;
Hoseini, S. Jafar ;
Montazerozohori, Morteza ;
Mehrabi, Rasool ;
Nasrabadi, Hasan .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 382 :99-105