Amberlyst-15, an efficient heterogeneous catalyst for the 1,4-dihydropyridine synthesis

Hung Quang Tran, Loan Thanh Thi Pham, Nhi Lan Thi Do, Phuc Van Ban, Hien Thanh Thi Nguyen, Tuan Thanh Dang, Tu Ngoc Duong, Dang Van Do, Hoan Xuan Vu

Abstract


The paper reported synthesizing 1,4-dihydropyridine (1,4-DHP) from β-ketoester, aromatic aldehyde, and ammonium acetate via a two-step, using heterogeneous catalyst Amberlyst-15 in high yields at room temperature. The method was applied to synthesize some 1,4-DHP derivatives. Moreover, the catalyst was reused at least five times without loss of catalytic activity under eco-friendly conditions.

Keywords


1,4-dihydropyridine; amberlyst-15; heterogeneous catalyst

Full Text:

PDF

References


D. J. Triggle, Biochem. Pharmacol. 74 (2007) 1-9. https://doi.org/10.1016/j.bcp.2007.01.016

F. Bossert, H. Meyer E. Wehinger, Angewandte Chemie International Edition in English 20 (1981) 762-769. https://doi.org/10.1002/anie.198107621

B. Loev, M. M. Goodman, M. K. Snader, R. Tedeschi E. Macko, J. Med. Chem. 17 (1974) 956-965. https://doi.org/10.1021/jm00255a010

D. Viradiya, S. Mirza, F. Shaikh, R. Kakadiya, A. Rathod, N. Jain, R. Rawal A. Shah, Anticancer Agents Med Chem 17 (2017) 1003-1013. https://doi.org/10.2174/1871520616666161206143251

A. Idhayadhulla, R. S. Kumar, A. J. A. Nasser, S. Kavimani S. Indhumathy, Pharm. Chem. J. 49 (2015) 463-466. https://doi.org/10.1007/s11094-015-1305-x

V. M. Gadotti, C. Bladen, F. X. Zhang, L. Chen, M. G. Gunduz, R. Simsek, C. Safak G. W. Zamponi, Pflugers Archiv : European journal of physiology 467 (2015) 2485-2493. https://doi.org/10.1007/s00424-015-1725-1

T. Takenaka, S. Usuda, T. Nomura, H. Maeno T. Sado, Arzneimittel-Forschung 26 (1976) 2172-2178.

R. S. Kumar, A. Idhayadhulla, A. J. Nasser, S. Kavimani S. Indumathy, Indian journal of pharmaceutical sciences 72 (2010) 719-725. https://doi.org/10.4103/0250-474X.84580

L. M. Tarasenko, K. S. Neporada V. Klusha, Bull. Exp. Biol. Med. 133 (2002) 369-371. https://doi.org/10.1023/a:1016250121896

R. Budriesi, P. Ioan, A. Locatelli, S. Cosconati, A. Leoni, M. P. Ugenti, A. Andreani, R. Di Toro, A. Bedini, S. Spampinato, L. Marinelli, E. Novellino A. Chiarini, J. Med. Chem. 51 (2008) 1592-1600. https://doi.org/10.1021/jm070681+

A. Hantzsch, Justus Liebig's Annalen der Chemie 215 (1882) 1-82. https://doi.org/10.1002/jlac.18822150102

M. De Luca, G. Ioele G. Ragno, Pharmaceutics 11 (2019) 85. https://doi.org/10.3390/pharmaceutics11020085

M. Baumann I. R. Baxendale, Beilstein J Org Chem 9 (2013) 2265-2319. https://doi.org/10.3762/bjoc.9.265

V. K. Sharma S. K. Singh, RSC Advances 7 (2017) 2682-2732. https://doi.org/10.1039/c6ra24823c

A. Debache, R. Boulcina, A. Belfaitah, S. Rhouati B. Carboni, Synlett 2008 (2008) 509-512. https://doi.org/10.1055/s-2008-1032093

L.-M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z.-Y. Fan, H. Tian C.-T. Qian, Tetrahedron 61 (2005) 1539-1543. https://doi.org/10.1016/j.tet.2004.11.079

S. R. Cherkupally R. Mekala, Chem Pharm Bull (Tokyo) 56 (2008) 1002-1004. https://doi.org/10.1248/cpb.56.1002

S. Ko, M. N. V. Sastry, C. Lin C.-F. Yao, Tetrahedron Lett. 46 (2005) 5771-5774. https://doi.org/10.1016/j.tetlet.2005.05.148

G. Sabitha, G. S. K. K. Reddy, C. S. Reddy J. S. Yadav, Tetrahedron Lett. 44 (2003) 4129-4131. https://doi.org/10.1016/s0040-4039(03)00813-x

N. Tewari, N. Dwivedi R. P. Tripathi, Tetrahedron Lett. 45 (2004) 9011-9014. https://doi.org/10.1016/j.tetlet.2004.10.057

J. H. Lee, Tetrahedron Lett. 46 (2005) 7329-7330. https://doi.org/10.1016/j.tetlet.2005.08.137

S. Ko C.-F. Yao, Tetrahedron 62 (2006) 7293-7299. https://doi.org/10.1016/j.tet.2006.05.037

G. V. Sharma, K. L. Reddy, P. S. Lakshmi P. R. Krishna, Synthesis 2006 (2006) 55-58. https://doi.org/10.1055/s-2005-921744

S. Paul, R. Gupta, R. Gupta A. Loupy, Synthesis 2007 (2007) 2835-2838. https://doi.org/10.1055/s-2007-983839

D. R. Patil D. S. Dalal, Lett. Org. Chem. 8 (2011) 477-483. https://doi.org/10.2174/157017811796504891

A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati B. Carboni, Tetrahedron Lett. 50 (2009) 5248-5250. https://doi.org/10.1016/j.tetlet.2009.07.018

F. Tamaddon, Z. Razmi A. A. Jafari, Tetrahedron Lett. 51 (2010) 1187-1189. https://doi.org/10.1016/j.tetlet.2009.12.098

X. Y. Wu, Synth. Commun. 42 (2011) 454-459. https://doi.org/10.1080/00397911.2010.525773

S. X. Wang, Z. Y. Li, J. C. Zhang J. T. Li, Ultrason. Sonochem. 15 (2008) 677-680. https://doi.org/10.1016/j.ultsonch.2008.02.009

H. Adibi, H. A. Samimi M. Beygzadeh, Catal. Commun. 8 (2007) 2119-2124. https://doi.org/10.1016/j.catcom.2007.04.022

M. Lei, L. Ma L. Hu, Synth. Commun. 41 (2011) 1969-1976. https://doi.org/10.1080/00397911.2010.494814

R. A. Sheldon R. S. Downing, Appl. Catal. A Gen. 189 (1999) 163-183. https://doi.org/10.1016/s0926-860x(99)00274-4

R. A. Sheldon J. Dakka, Catal. Today 19 (1994) 215-245. https://doi.org/10.1016/0920-5861(94)80186-x

S. Palaniappan A. John, J. Mol. Catal. A: Chem. 233 (2005) 9-15. https://doi.org/10.1016/j.molcata.2005.02.002

M. Maheswara, V. Siddaiah, Y. K. Rao, Y.-M. Tzeng C. Sridhar, J. Mol. Catal. A: Chem. 260 (2006) 179-180. https://doi.org/10.1016/j.molcata.2006.07.024

A. M. Zonouz S. B. Hosseini, Synth. Commun. 38 (2008) 290-296. https://doi.org/10.1080/00397910701750003

E. Rafiee, S. Eavani, S. Rashidzadeh M. Joshaghani, Inorg. Chim. Acta 362 (2009) 3555-3562. https://doi.org/10.1016/j.ica.2009.03.049

A. Hantzsch, Ber. Dtsch. Chem. Ges. 14 (1881)

-1638. https://doi.org/10.1002/cber.18810140214

D. Elhamifar, H. Khanmohammadi D. Elhamifar, RSC Advances 7 (2017) 54789-54796. https://doi.org/10.1039/c7ra10758g

S. Baluja R. Talaviya, Int. J. Pharm., Chem. Biol. Sci. 5 (2015).

E. F. V. Scriven, Pyridines: From Lab to Production, Elsevier Science, 2013.

M. Filipan-Litvić, M. Litvić, I. Cepanec V. Vinković, Molecules 12 (2007) 2546-2558. https://doi.org/10.3390/12112546

P. A. Hopes, A. J. Parker I. Patel, Org. Process Res. Dev. 10 (2006) 808-813. https://doi.org/10.1021/op060057r

P. F. Siril, H. E. Cross D. R. Brown, J. Mol. Catal. A: Chem. 279 (2008) 63-68. https://doi.org/10.1016/j.molcata.2007.10.001

E. K. Ekinci, G. Gündüz N. Oktar, Int. J. Chem. React. Eng. 14 (2016) 309-314. https://doi.org/10.1515/ijcre-2015-0012

N. I. Guzman Barrera, C. Bories, J. Peydecastaing, C. Sablayrolles, E. Vedrenne, C. Vaca-Garcia S. Thiebaud-Roux, Green Sustain. Chem. 8 (2018) 221-246. https://doi.org/10.4236/gsc.2018.83016




DOI: https://doi.org/10.51316/jca.2022.075

Refbacks

  • There are currently no refbacks.




*******

Index: Google Scholar; Crossref

---------

Vietnam Journal of Catalysis and Adsorption

Address: Room 302  |  C4-5  |  Hanoi University of Science and Technology. 1 Dai Co Viet, Hanoi.

Tel.: ‎‎‎+84. 967.117.098 (Dr. Phượng)  |  Email: editor@jca.edu.vn  |  FB: JCA.VNACA