Abstract
Synthesis of new 8-alkyl-5-aryl-1,3-dimethyl-5,7-dihydro-2H-pyrimido[5′,4′:5,6]pyrano[2,3-d]- pyrimidine-2,4,6(1H,3H)-triones by the high yield reaction of 7-amino-5-aryl-1,3-dimethyl-2,4-dioxo-1,3,4,5- tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitriles with aliphatic carboxylic acids in the presence of POCl3 is presented. It is probable that synthesis of these new products proceeds via the tandem intramolecular Pinner–Dimroth rearrangement. The products are characterized by FT-IR, 1H, and 13C NMR spectra and evaluated for their antibacterial activity against gram +ve bacteria (Staphylococcus aureus and Staphylococcus epidermidis) and gram–ve bacteria (Escherichia coli and Pseudomonas aeruginosa) using the disc diffusion method.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Singh, K. and Kaur, T., Med. Chem. Comm. 2016, vol. 7, p. 749. doi https://doi.org/10.1039/c6md00084c
Kumar, B.S., Lakshmi, P.V.A., Veena, B.S., and Sujatha, E., Russ. J. Gen. Chem. 2017, vol. 87, p. 829. doi https://doi.org/10.1134/S1070363217040260
Kabeer, S.A., Reddy, G.R., Sreelakshmi, P., Manidhar, D.M., and Reddy, C.S., J. Heterocycl. Chem., 2017, vol. 54, p. 2598. doi https://doi.org/10.1002/jhet.2856
Elkanzi, N.A.A., Morsy, N.M., Aly, A.A., Brown, A.B., and Ramadan, M., J. Heterocycl. Chem., 2016, vol. 53, p. 1838. doi https://doi.org/10.1002/jhet.2495
Atapour-Mashhad, H., Tayarani-Najaran, Z., Davoodnia, A., Moloudi, R., and Mousavi, S.H., Drug Chem. Toxicol. 2011, vol. 34, p. 271. doi https://doi.org/10.3109/01480545.2010.545066
Atapour-Mashhad, H., Soukhtanloo, M., Massoudi, A., Shiri, A., Parizadeh, S.M., and Bakavoli, M., J. Heterocycl. Chem., 2017, vol. 54, p. 366. doi https://doi.org/10.1002/jhet.2592
Desai, N.C., Kotadiya, G.M., and Trivedi, A.R., Bioorg. Med. Chem. Lett. 2014, vol. 24, p. 3126. doi https://doi.org/10.1016/j.bmcl.2014.05.002
Qin, X., Liu, X., Hong-Bo, L., Li-Na, Y., and Xiaoya, H., Biosens. Bioelectron. 2013, vol. 42, p. 355. doi https://doi.org/10.1016/j.bios.2012.11.004
Zeidler, J., Sayer, B.G., and Spenser, I.D., J. Am. Chem. Soc., 2003, vol. 125, p. 13094. doi https://doi.org/10.1021/ja030261j
Kumar, A.K.A., Bodke, Y.D., Sambasivam, G., and Lakra, P.S., Monatsh. Chem. 2017, vol. 148, p. 1767. doi https://doi.org/10.1007/s00706-017-1943-7
Chikhale, R., Thorat, S., Choudhary, R.K., Gadewal, N., and Khedekar, P., Bioorg. Chem. 2018, vol. 77, p. 84. doi https://doi.org/10.1016/j.bioorg.2018.01.008
Pai, A., Jayashree, B.S., Jeyaprakash, R.S., Kini, S.G., and Lobo, R., Lat. Am. J. Pharm. 2017, vol. 36, p. 1568.
Mule, S.N.R., Nurbhasha, S., Kolla, J.N., Jadav, S.S., Jayaprakash, V., Bhavanam, L.R., and Bollikolla, H.B., Med. Chem. Res. 2016, vol. 25, p. 2534. doi https://doi.org/10.1007/s00044-016-1668-x
Chechina, N.V., Kolos, N.N., Omelchenko, I.V., and Musatov, V.I., Chem. Heterocycl. Compd. 2018, vol. 54, p. 58. doi https://doi.org/10.1007/s10593-018-2230-1
Davoodnia, A., Bakavoli, M., Bashash, M., Roshani, M., and Zhiani, R., Turk. J. Chem. 2007, vol. 31, p. 599.
Jubeen, F., Iqbal, S.Z., Shafiq, N., Khan, M., Parveen, S., Iqbal, M., and Nazir, A., Synth. Commun. 2018, vol. 48, p. 601. doi https://doi.org/10.1080/00397911.2017.1408840
Rimaz, M., Mirshokraie, A., Khalili, B., and Motiee, P., Arkivoc 2015, vol. 2015, p. 88. doi https://doi.org/10.3998/ark.5550190.p008.896
Rimaz, M., Rabiei, H., Khalili, B., and Prager, R.H., Aust.J. Chem. 2014, vol. 67, p. 283. doi https://doi.org/10.1071/CH13438
Fedorova, E.V., Kvasha, V.V., Studentsov, E.P., Moskvin, A.V., and Ivin, B.A., Russ. J. Gen. Chem. 2007, vol. 77, p. 589. doi https://doi.org/10.1134/S1070363207040159
Kidwai, M., Goyal, R., and Singhal, K., Indian J. Chem. B 2007, vol. 46, p. 1159. doi Not available
Roshani, M., Davoodnia, A., Shaker Hedayat, M., and Bakavoli, M., Phosphorus Sulfur Silicon Relat. Elem. 2004, vol. 179, p. 1153. doi https://doi.org/10.1080/10426500490459759
Davoodnia, A., Bakavoli, M., Mohseni, S., and Tavakoli-Hoseini, N., Monatsh. Chem. 2008, vol. 139, p. 963. doi https://doi.org/10.1007/s00706-007-0844-6
Davoodnia, A., Bakavoli, M., Moloudi, R., Khashi, M., and Tavakoli-Hoseini, N., Chin. Chem. Lett. 2010, vol. 21, p. 1. doi https://doi.org/10.1016/j.cclet.2009.09.002
Davoodnia, A., Khashi, M., and Tavakoli-Hoseini, N., Chin. J. Catal. 2013, vol. 34, p. 1173. doi https://doi.org/10.1016/S1872-2067(12)60547-6
Davoodnia, A., Khashi, M., Tavakoli-Hoseini, N., Moloudi, R., and Zamani, H.A., Monatsh. Chem. 2013, vol. 144, p. 677. doi https://doi.org/10.1007/s00706-012-0847-9
Khashi, M., Davoodnia, A., and Chamani, J., Phosphorus Sulfur Silicon Relat. Elem. 2014, vol. 189, p. 839. doi https://doi.org/10.1080/10426507.2013.858253
Gholipour, S., Davoodnia, A., and Nakhaei-Moghaddam, M., Chem. Heterocycl. Compd. 2015, vol. 51, p. 808. doi https://doi.org/10.1007/s10593-015-1779-1
Tajfirooz, F., Davoodnia, A., Pordel, M., Ebrahimi, M., and Beyramabadi, S.A., Russ. J. Gen. Chem. 2017, vol. 87, p. 2429. doi https://doi.org/10.1134/S1070363217100255
Fattahi, M., Davoodnia, A., and Pordel, M., Russ. J. Gen. Chem. 2017, vol. 87, p. 863. doi https://doi.org/10.1134/S1070363217040326
Khoramdelan, F., Davoodnia, A., Bozorgmehr, M.R., and Ebrahimi, M., Russ. J. Gen. Chem. 2017, vol. 87, p. 2961. doi https://doi.org/10.1134/S1070363217120386
Hosseininasab, N., Davoodnia, A., Rostami-Charati, F., Tavakoli-Hoseini, N., and Khojastehnezhad, A., J. Heterocycl. Chem., 2018, vol. 55, p. 161. doi https://doi.org/10.1002/jhet.3019
Gholipour, S., Davoodnia, A., and Nakhaei-Moghaddam, M., Der. Pharma. Chemica. 2015, vol. 7, p. 368.
Tang, J.H., Shi, D.X., Zhang, L.J., Zhang, Q., and Li, J.R., Synth. Commun. 2010, vol. 40, p. 632. doi https://doi.org/10.1080/00397910902908822
Chai, H., Li, J., Yang, L., Lu, H., Qi, Z., and Shi, D., RSC Adv., 2014, vol. 4, p. 44811. doi https://doi.org/10.1039/c4ra08031a
Karimi, N., Davoodnia, A., and Pordel, M., Heterocycl. Commun. 2018, vol. 24, p. 31. doi https://doi.org/10.1515/hc-2017-0228
Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Susceptibility Testing Twentieth Informational Supplement. Clinical and Laboratory Standards Institute, Wayne, P.A, CLSI document M100-S20. Available at: http://www.clsi.org (Accessed October 22, 2018).
Author information
Authors and Affiliations
Corresponding author
Additional information
The text was submitted by the authors in English.
Rights and permissions
About this article
Cite this article
Asadian, M., Davoodnia, A. & Beyramabadi, S.A. Efficient Synthesis of New Pyrimido[5′,4′:5,6]pyrano[2,3-d]pyrimidine-2,4,6(1H,3H)-triones via the Tandem Intramolecular Pinner–Dimroth Rearrangement, and Their Antibacterial Activity. Russ J Gen Chem 88, 2658–2663 (2018). https://doi.org/10.1134/S1070363218120290
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363218120290