Nanocrystalline copper(II) oxide-catalyzed one-pot synthesis of imidazo[1,2-a]quinoline and quinolino[1,2-a]quinazoline derivatives via a three-component condensation

Synthetic Communications

Volumn 41, Issue 3, 2011, Pages 426-435

  Ahmadi, Seyed Javad ^a   Hosseinpour, Morteza ^b   Sadjadi, Sodeh ^a  

^a NUCLEAR SCIENCE AND TECHNOLOGY RESEARCH INSTITUTE   (Iran)

^b SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

CuO nanoparticles; imidazo 1 2 a quinoline; quinolino 1 2 a quinoline

Indexed keywords

COPPER OXIDE; IMIDAZO[1,2 A]QUINOLINE DERIVATIVE; NANOCRYSTAL; QUINAZOLINE DERIVATIVE; QUINOLINE DERIVATIVE; QUINOLINO[1,2 A]QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ONE POT SYNTHESIS;

EID: 78751533290     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903576693     Document Type: Article

References (30)

1. Sharma, S.; Saha, B.; Sawant, D.; Kundu, B. Synthesis of novel N-rich polycyclic skeletons based on azoles and pyridines. J. Comb. Chem. 2007, 9, 783-792.
2. Gryglewicz, S. Rapeseed oil methyl esters preparation using heterogeneous catalysts. Bioresource. Technol. 1999, 70, 249-253.
3. Tanabe, K.; Hoelderich, W. F. Industrial application of solid acid-base catalysts. Appl. Catal. 1999, 181, 399-434.
4. Corma, A.; Hamid, A.; Iborra, S.; Velty, A. Lewis and Brønsted basic active sites on solid catalysts and their role in the synthesis of monoglycerides. J. Catal. 2005, 234, 340-347.
5. Ono, Y. Solid base catalysts for the synthesis of fine chemicals. J. Catal. 2003, 216, 406-415.
6. Schachter, Y.; Herman, P. Calcium-oxide-catalyzed reactions of hydrocarbons and of alcohols. J. Catal. 1968, 11, 147-158.
7. Xie, W.; Peng, H.; Chen, L. Transesterification of soybean oil catalyzed by potassium loaded on alumina as a solid-base catalyst. Appl. Catal. 2006, 300, 67-74.
8. Supes, G. J.; Dasari, M. A.; Doskocil, E. J.; Mankidy, P. J.; Goff, M. J. Transesterifica-tion of soybean oil with zeolite and metal catalysts. Appl. Catal. 2004, 257, 213-223.
9. Zhang, G.; Hattori, H.; Tanabe, K. Aldol addition of acetone, catalyzed by solid base catalysts: Magnesium oxide, calcium oxide, strontium oxide, barium oxide, lanthanum(III) oxide, and zirconium oxide. Appl. Catal. 1988, 36, 189-197.
10. Iizuka, T.; Hattori, H.; Ohno, Y.; Sohma, J.; Tanabe, K. Basic sites and reducing sites of calcium oxide and their catalytic activities. J. Catal. 1971, 22, 130-139.
11. Kabashima, H.; Katou, T.; Hattori, H. Conjugate addition of methanol to 3-buten-2-one over solid base catalysts. Appl. Catal. 2001, 214, 121-124.
12. Poizot, P.; Laruelle, S.; Grugeon, S.; Dupont, L.; Tarascon, J. M. Nano-sized transition-metal oxides as negative-electrode materials for lithium-ion batteries. Nature 2000, 407, 496-499.
13. 2 catalysts. Catal. Today 2004, 93-95, 241-246.
14. Kantam, M. L.; Laha, S.; Yadav, J.; Lihkar, P. R.; Sreedhar, B.; Choudary, B. M. Asymmetric hydrosilylation of prochiral ketones catalyzed by nanocrystalline copper(II) oxide. Adv. Synth. Catal. 2007, 349, 1797-1802.
15. Kantam, M. L.; Laha, S.; Yadav, J.; Bhargava, S. An efficient synthesis of propargyla-mines via three-component coupling of aldehydes, amines, and alkynes catalyzed by nano-crystalline copper(II) oxide. Tetrahedron Lett. 2008, 49, 3083-3086.
16. Kantam, M. L.; Ramani, T.; Chakrapani, L.; Kumar, K. V. Direct asymmetric aldol reactions catalyzed by nanocrystalline copper(II) oxide. Tetrahedron Lett. 2008, 49, 1498-1501.
17. Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R. Copper oxide nanoparticle-catalyzed coupling of diaryl diselenide with aryl halides under ligand-free conditions. Org. Lett. 2009, 11 (4), 951-953.
18. Song, Y.-J.; Yoo, C.; Hong, J.-T.; Kim, S.-J.; Seung, U. S.; Jang, H.-Y. Nanocrystalline copper oxide(II)-catalyzed alkyne-azide cycloadditions. B. Kor. Chem. Soc. 2008, 29 (8), 1561-1564.
19. Rout, L.; Jammi, S.; Punniyamurthy, T. Novel CuO nanoparticle-catalyzed C-N cross coupling of amines with iodobenzene. Org. Lett. 2007, 9 (17), 3397-3399.
20. 2=polypyrrole). Synth. Met. 1999, 102, 1238-1239.
21. Hui, W.; Xu, J.-Z.; Zhu, J.-J. Chen, H.-Y. Preparation of CuO nanoparticles by microwave irradiation. J. Cryst. Growth 2002, 244, 88-94.
22. Ray, S. C. Preparation of copper oxide thin film by the sol-gel-like dip technique and study of their structural and optical properties. Sol. Energy Mater. Sol. Cells 2001, 68, 307-312.
23. (a) Jiang, Z.; Niu, Q.; Deng, W. Hydrothermal synthesis of CuO nanostructures with novel shapes. Nanoscience 2007, 12, 40-44
24. (b) Volanti, D. P.; Keyson, D.; Cavalcante, L. S.; Simoes, A. Z.; Joya, M. R.; Longo, E.; Varela, J. A.; Pizani, P. S.; Souza, A. G. Synthesis and characterization of CuO flower-nanostructure processing by a domestic hydrothermal microwave. J. Alloy. Compd. 2008, 459, 537-542. (Pubitemid 351680629)
25. Song, X. Y.; Yu, H. Y.; Sun, S. X. Single-crystalline CuO nanobelts fabricated by a convenient rout. J. Colloid Int. Sci. 2005, 289, 588-591.
26. Li, D.; Leung, Y. H.; Djurisic, A. B.; Liu, Z. T.; Xie, M. H.; Gao, J.; Chan, W. K. CuO nanostructures prepared by a chemical method. J. Cryst. Growth 2005, 282, 105-111.
27. 2 and CuO nanostructures. J. Phys. Chem. B 2004, 108, 17825-17831.
28. Ahmadi, S. J.; Sadjadi, S.; Hosseinpour, M.; Outokesh, M.; Hekmatshoar, R. A heterogeneous strong basic nanocrystalline copper(II) oxide catalyst for efficient synthesis of 4-keto-4,5,6,7-tetrahydrobenzofurans. Catal. Commun. 2009, 10, 1423-1426.
29. Kantam, M. L.; Laha, S.; Yadav, J.; Bhargava, S. An efficient synthesis of propargyla-mines via three-component coupling of aldehydes, amines and alkynes catalyzed by nano-crystalline copper(II) oxide. Tetrahedron Lett. 2008, 49, 3083-3086.
30. Tu, S.; Li, C.; Li, G.; Cao, L.; Shao, Q.; Zhou, D.; Jiang, B.; Zhou, J.; Xia, M. Microwave-assisted combinatorial synthesis of polysubstituent imidazo[1,2-a]quinoline, pyrimido[1,2-a]quinoline and quinolino[1,2-a] quinazoline derivatives. J. Comb. Chem. 2007, 9, 1144-1148.