N-sulfonic acid pyridinium-4-carboxylic acid chloride as a novel and efficient catalyst for the condensation reaction of aldehyde with thiobarbituric acid and ammonium acetate
محورهای موضوعی : Iranian Journal of CatalysisAhmad Reza Moosavi-Zare 1 , Hadis Afshar-Hezarkhani 2
1 - Department of Chemistry, Sayyed Jamaleddin Asadabadi University, Asadabad, 6541861841, Iran.
2 - Department of Chemistry, Sayyed Jamaleddin Asadabadi University, Asadabad, 6541861841, Iran.
کلید واژه: Solvent-free, aldehyde, Ionic liquid, ammonium acetate, N-sulfonic acid pyridinioum-4-carboxylic acid chloride, Pyrido[2, 3-d:6, 5-d]dipyrimidine, 2-thiobarbituric acid,
چکیده مقاله :
N-sulfonic acid pyridinium -4-carboxylic acid chloride {[Pyridine-N-SO3H-4-COOH]Cl} was synthesized, identified and applied as an effective catalyst for the preparation of pyrido[2,3-d:6,5-d]dipyrimidines by the condensation reaction of various aldehyde with 2-thiobarbituric acid and ammonium acetate under solvent-free conditions.The structure ofcatalyst was studied by various techniques including FT-IR, 1HNMR, 13CNMR, SEM, EDS, TEM, TGA, DTG and XRD analyses.
[1] M. Mohsenimehr, M. Mamaghani, F. Shirini, M. Sheykhan, F. Azimian Moghaddam, Chin. Chem. Lett. 25 (2014) 1387-1391.
[2] L. Yang, D. Shi, S. Chen, H. Chai, D. Huang, Q. Zhang, J. Li, Green Chem. 14 (2012) 945-951.
[3] I. D. Bystryakova, O. A. Burova, G. M. Chelysheva, S. V. Zhilinkova, N. M. Smirnova, T. S. Safonova, Pharm. Chem. J. 25 (1991) 874-876.
[4] I. O. Donkor, C. L. Klein, L. Liang, N. Zhu, E. Bradley, A. M. Clark, J. Pharm. Sci. 84 (1995) 661-664.
[5] E. M. Grivsky, S. Lee, C. W Sigel, D. S Duch, C. A Nichol, J. Med. Chem. 23 (1980) 327-331.
[6] V. E. Kolla, A. B. Deyanov, F. Y. Nazmetdinov, Z. N. Kashina, L. P. Drovosekova, Pharm. Chem. J. 27 (1993) 635-636.
[7] A. M. Thompson, A. J. Bridges, D. W. Fry, A. J. Kraker, W. A. Denny, J. Med. Chem. 38 (1995) 3780-3788.
[8] N. Kammasud, C. Boonyarat, K. Sanphanya, M. Utsintong, S. Tsunoda, H. Sakurai, I. Saiki, I. André, D. S. Grierson, O. Vajragupta, Bioorg. Med. Chem. Lett. 19 (2009) 745-750.
[9] A. Pastor, R, Alajarin, J. J. Vaquero, J. Alvarez-Builla, M. F. D. Casa-Juana, C. Sunkel, Jaime, G. Priego, I. Fonseca, J. Sanz-Aparicio, Tetrahedron 50 (1994) 8085-8098.
[10] C. J. C. Connolly, J. M. Hamby, M. C. Schroeder, M. Barvian, G. H. Lu, R. L. Panek, A. Amar, C, Shen, A. J. Kraker, D. W. Fry, W. D. Klohs, A. M. Doherty, Med. Chem. Lett. 7 (1997) 2415-2420.
[11] A. M. Thompson, A. M. Delaney, J. M. Hamby, M. C. Schroeder, T. A. Spoon, S. M. Crean, H. D. H. Showalter, W. A. Denny, J. Med. Chem. 48 (2005) 4628-4653.
[12] L. L. Corre, A.-L. Girard, J. Aubertin, F. Radvanyi, C. Benoist-Lasselin, A. Jonquoy, E. Mugniery, L. Legeai-Mallet, P. Busca, Y. L. Merrer, Org. Biomol. Chem. 8 (2010) 2164-2173.
[13] A. Bazgir, M. M. Khanaposhtani, R. Ghahremanzadeh, A. A. Soorki, C. R. Chim. 12 (2009) 1287-1295.
[14] M. Kidwai, R. Mohan, S. Saxena, Russ. Chem. Bull. Int. Ed. 52 (2003) 2457-2460.
[15] G.-W. Wang, C.-B. Miao, Green Chem. 8 (2006) 1080-1085.
[16] H. Naeimi, A. Didar, Ultrason. Sonochem. 34 (2017) 889-895.
[17] H. Naeimi, V. Didar, Z. Rashid, Z. Zahraie, J. Antibiot. 70 (2017) 845–852.
[18] a) M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, Org. Prep. Proced. Int. 42 (2010) 95-102. b) A. R. Moosavi-Zare, M. Pouraskar-Borazjani, Z. Naz, Iran. Chem. Commun. 2 (2014) 168-172.
[19] S. Mohammadi-Aghdam, H. Jabbari, O. Pouralimardan, F. Divsar, I. Amini, S. Sajjadifar, Iran. Chem. Commun. 6 (2018) 423-436.
[20] A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, A. Zare, Sci. Iran. Trans. C 17 (2010) 31-36.
[21] a) M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, H. G. Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem-Rostami, J. Org. Chem. 77 (2012) 3640-3645. b) M. Zarei, E. Noroozizadeh, A. R. Moosavi-Zare, M. A. Zolfigol, J. Org. Chem. 83 (2018) 3645-3650. c) A. R. Moosavi-Zare, M. A. Zolfigol, M. Zarei, E. Noroozizadeh, M. H. Beyzavi, RSC Adv. 6 (2016) 89572-89577.
[22] M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A 400 (2011), 70-81.
[23] A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, A. Zare, E. Ghaemi, V. Khakyzadeh, Z. Asgari, A. Hasaninejad, Sci. Iran. Trans. C 18 (2011) 1365-1371.
[24] M. A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, A. Zare, S. B. Azimi, Z. Asgari, A. Hasaninejad, C. R. Chim. 15 (2012) 719-736.
[25] A. Zare, T. Yousofi, A. R. Moosavi-Zare, RSC Adv. 2 (2012) 7988-7991.
[26] A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, Z. Asgari, M. Shekouhy, A. Zare, A. Hasaninejad, RSC Adv. 2 (2012) 8010-8013.
[27] M. A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, G. Chehardoli, F. Derakhshan-Panah, A. Zare, O. Khaledian, Sci. Iran. Trans. C 19 (2012) 1584-1590.
[28] M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, Z. Asgari, V. Khakyzadeh, A. Hasaninejad, J. Ind. Eng. Chem. 19 (2013) 721-726.
[29] A. Zare, J. Sanjideh, Iran. Chem. Commun. 6 (2018) 416-422.
[30] A. Zare, F. Abi, A. R. Moosavi-Zare, M. H. Beyzavi, M. A. Zolfigol, J. Mol. Liq. 178 (2013) 113-121.
[31] a) A. R. Moosavi-Zare, M. A. Zolfigol, F. Derakhshan-Panah, S. Balalaie, Mol. Catal. 449 (2018) 142-151. b) A. R. Moosavi-Zare, M. A. Zolfigol, M. Daraei, Synlett. 25 (2014) 1173-1177.
[32] a) P. C. B. Page, M. M. Farah, B. Buckley, R. A. Blacker, J. Org. Chem. 72 (2007) 4424-4430. b) J. Marco-Martinez, V. Marcos, S. Reboredo, S. Filippone, N. Martin, Angew. Chem. Int. Ed. 52 (2013) 5115-5119. c) R. Gramage-Doria, J. N. H. Reek, ChemCatChem. 5 (2013) 677-679.
[33] V. Polshettiwar, R. S. Varma, Green Chem. 12 (2010) 743-754.
[34] H. Naeimi, Z. S. Nazifi, Iran. J. Catal. 8 (2018) 249-255.
[35] G. M. Ziarani, H. Mollabagher, P. Gholamzadeh, A. Badiei, F. Yazdian, Iran. J. Catal. 8 (2018) 59-67.
[36] N. Gupta, P. Bhardwaj, G. Sharma, Iran. J. Catal. 7 (2017) 243-248.
[37] H. Naeimi, V. Nejadshafiee, M. R. Islami, Microporous Mesoporous Mater. 227 (2016) 23-30.
[38] H. Naeimi, K. Rabiei, Ultrason. Sonochem. 19 (2012) 130-135.
[39] A. Zare, A. Kohzadian, Z. Abshirini, S. S. Sajadikhah, J. Phipps, M. Benamarad, M. H. Beyzavi, New J. Chem. 43 (2019) 2247-2257.
