Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 53, 2023 - Issue 11
127
Views
3
CrossRef citations to date
0
Altmetric
Articles

Water mediated pot, atom, and step economic (PASE) synthesis of pyrimido[4,5-d]pyrimidines using ultrasound and microwave irradiation approaches

, &
Pages 823-834 | Received 03 Dec 2022, Published online: 12 Apr 2023

References

  • Kalita, S. J.; Mecadon, H.; Deka, D. C. Pot, Atom and Step Economic (PASE) Synthesis of 5-Monoalkylbarbiturates through Domino aldol-Michael Reaction. Tetrahedron Lett. 2015, 56, 731–734. DOI: 10.1016/j.tetlet.2014.12.091.
  • Trivedi, H. D.; Joshi, V. B.; Patel, B. Y. Pyrazole Bearing Pyrimidine Analogues as the Privileged Scaffolds in Antimicrobial Drug Discovery: A Review. Anal. Chem. Lett. 2022, 12, 147–173. DOI: 10.1080/22297928.2021.1910565.
  • Desai, N. C.; Patel, B. Y.; Jadeja, K. A.; Patel, B. P. Landscaping of Quinoline Based Heterocycles as Potential Antimicrobial Agents: A Mini Review. NAPDD 2017, 1, 555570. DOI: 10.19080/NAPDD.2017.01.555570.
  • Desai, N.; Vaghani, H.; Patel, B. Y.; Karkar, T. Synthesis and Antimicrobial Activity of Fluorine Containing Pyrazole-Clubbed Dihydropyrimidinones. Pharm. Sci. 2018, 80, 242. DOI: 10.4172/pharmaceutical-sciences.1000351.
  • Patel, B. Y.; Karkar, T. J.; Bhatt, M. J. Synthesis of 5-Substituted-1,3,4-Oxadiazole Clubbed Pyrazole and Dihydropyrimidine Derivatives as Potent Bioactive Agents. ECB 2021, 10, 13. DOI: 10.17628/ecb.2021.10.13-20.
  • Desai, N. C.; Vaghani, H. V.; Karkar, T. J.; Patel, B. Y.; Jadeja, K. A. Synthesis and Antimicrobial Studies of 1,2,3,4-Tetrahydropyrimidine Bearing Imidazole Analogues. Indian J. Chem. B 2017, 56, 438. http://nopr.niscair.res.in/handle/123456789/41188.
  • Trivedi, H. D.; Patel, B. Y.; Patel, P. K.; Sagar, S. R. Synthesis, Molecular Modeling, ADMET and Fastness Studies of Some Quinoline Encompassing Pyrimidine Azo Dye Derivatives as Potent Antimicrobial Agents. Chem. Data Collect. 2022, 41, 100923. DOI: 10.1016/j.cdc.2022.100923.
  • Desai, N. C.; Patel, B. Y.; Dave, B. P. Synthesis and Antimicrobial Activity of Novel Quinoline Derivatives Bearing Pyrazoline and Pyridine Analogues. Med. Chem. Res. 2017, 26, 109–119. DOI: 10.1007/s00044-016-1732-6.
  • Desai, N. C.; Patel, B. Y.; Dave, B. P. Approach for the Synthesis of Potent Antimicrobials Containing Pyrazole, Pyrimidine and Morpholine Analogues. ILCPA 2016, 69, 87–96. DOI: 10.18052/www.scipress.com/ILCPA.69.87.
  • Desai, N. C.; Bhatt, N.; Dodiya, A.; Karkar, T.; Patel, B.; Bhatt, M. Synthesis, Characterization and Antimicrobial Screening of Thiazole Based 1,3,4-Oxadiazoles Heterocycles. Res. Chem. Intermed. 2016, 42, 3039–3053. DOI: 10.1007/s11164-015-2196-x.
  • Desai, N. C.; Shihory, N.; Bhatt, M.; Patel, B.; Karkar, T. Studies on Antimicrobial Evaluation of Some 1-((1-(1H-Benzo[d]Imidazol-2-yl)Ethylidene)Amino)-6-((Arylidene)Amino)-2-Oxo-4-Phenyl-1,2-Dihydropyridine-3,5-Dicarbonitriles. Synth. Commun. 2015, 45, 2701–2711. DOI: 10.1080/00397911.2015.1102286.
  • Cruz, S. J.; de Aguiar, P. A. Overview of the Biological Activities of Pyrimido[4,5-d]Pyrimidines. Mini Rev. Med. Chem. 2021, 21, 2138–2168. DOI: 10.2174/1389557521666210219160115.
  • Beingessner, R. L.; Fan, Y.; Fenniri, H. Molecular and Supramolecular Chemistry of Rosette Nanotubes. RSC Adv. 2016, 6, 75820–75838. DOI: 10.1039/C6RA16315G.
  • Venkatesh, T.; Upendranath, K.; Manjanna, J. Optical, Electrochemical and DFT Studies of Indol-5,8-Pyrimido[4,5-d]Pyrimidine Derivatives. Chem. Data Collect. 2022, 40, 100886. DOI: 10.1016/j.cdc.2022.100886.
  • Monier, M.; Abdel-Latif, D.; El-Mekabaty, A.; Elattar, K. M. Bicyclic 6 + 6 Systems: The Chemistry of Pyrimido[4,5-d]Pyrimidines and Pyrimido[5,4-d]Pyrimidines. RSC Adv. 2019, 9, 30835–30867. DOI: 10.1039/C9RA05687D.
  • Desai, N. C.; Maheta, A. S.; Rajpara, K. M.; Joshi, V. V.; Vaghani, H. V.; Satodiya, H. M. Green Synthesis of Novel Quinoline Based Imidazole Derivatives and Evaluation of Their Antimicrobial Activity. J. Saudi Chem. Soc. 2014, 18, 963–971. DOI: 10.1016/j.jscs.2011.11.021.
  • Puri, S.; Kaur, B.; Parmar, A.; Kumar, H. Applications of Ultrasound in Organic Synthesis-A Green Approach. COC 2013, 17, 1790–1828. DOI: 10.2174/13852728113179990018.
  • Eskandari, K.; Karami, B.; Farahi, M.; Mouzari, V. Silica Sodium Carbonate Catalyzed in Water Synthesis of Novel Benzylbarbiturocoumarin Derivatives. Tetrahedron Lett. 2016, 57, 487–491. DOI: 10.1016/j.tetlet.2015.12.065.
  • Sukanya, S. H.; Venkatesh, T.; Rao, S. A.; Joy, M. N. Efficient L-Proline Catalyzed Synthesis of Some New (4-Substituted-Phenyl)-1,5-Dihydro-2H-Pyrimido[4,5-d][1,3]Thiazolo[3,2a]-Pyrimidine-2,4(3H)-Diones Bearing Thiazolopyrimidine Derivatives and Evaluation of Their Pharmacological Activities. J. Mol. Struct. 2022, 1247, 131324. DOI: 10.1016/j.molstruc.2021.131324.
  • Rimaz, M.; Khalafy, J.; Mousavi, H. A Green Organocatalyzed One-Pot Protocol for Efficient Synthesis of New Substituted Pyrimido[4,5-d]Pyrimidinones Using a Biginelli-like Reaction. Res. Chem. Intermed. 2016, 42, 8185–8200. DOI: 10.1007/s11164-016-2588-6.
  • Santosh, R.; Paul, P.; Selvam, M. K.; Raril, C.; Krishna, P. M.; Manjunatha, J. G.; Nagaraja, G. K. One-Pot Synthesis of Pyrimido[4,5-d]Pyrimidine Derivatives and Investigation of Their Antibacterial, Antioxidant, DNA-Binding and Voltammetric Characteristics. ChemistrySelect 2019, 4, 990–996. DOI: 10.1002/slct.201803416.
  • Shi, F.; Zhou, D.; Tu, S.; Li, C.; Cao, L.; Shao, Q. Pot, Atom and Step Economic Synthesis of Fused Three Heterocyclic Ring Compounds under Microwave Irradiation in Water. J. Heterocycl. Chem. 2008, 45, 1305–1310. DOI: 10.1002/jhet.5570450508.
  • Kitanosono, T.; Kobayashi, S. Reactions in Water Involving the “On‐Water” Mechanism. Chemistry 2020, 26, 9408–9429. DOI: 10.1002/chem.201905482.
  • Cortes-Clerget, M.; Yu, J.; Kincaid, J. R. A.; Walde, P.; Gallou, F.; Lipshutz, B. H. Water as the Reaction Medium in Organic Chemistry: From Our Worst Enemy to Our Best Friend. Chem. Sci. 2021, 12, 4237–4266. DOI: 10.1039/D0SC06000C.
  • Arafa, W. A. A.; Faty, R. A. M.; Mourad, A. K. A New Sustainable Strategy for Synthesis of Novel Series of Bis-Imidazole and Bis-1,3-Thiazine Derivatives: An Eco-Friendly Synthesis of Novel Series of Bis. J. Heterocycl. Chem. 2018, 55, 1886–1894. DOI: 10.1002/jhet.3221.
  • Mirhosseini‐Eshkevari, B.; Ghasemzadeh, M. A.; Esnaashari, M.; Ganjali, S. T. Introduction of a Novel Brønsted Acidic Ionic Liquid Incorporated in UiO‐66 Nanocages for the Efficient Synthesis of Pyrimido[4,5‐d]Pyrimidines. ChemistrySelect 2019, 4, 12920–12927. DOI: 10.1002/slct.201903642.
  • Safari, N.; Shirini, F.; Tajik, H. Verjuice as a Green and Bio-Degradable Solvent/Catalyst for Facile and Eco-Friendly Synthesis of 5-Arylmethylenepyrimidine-2,4,6-Trione, Pyrano[2,3-d]Pyrimidinone and Pyrimido[4,5-d]Pyrimidinone Derivatives. J. Iran. Chem. Soc. 2019, 16, 887–897. DOI: 10.1007/s13738-018-1565-y.
  • Shirini, F.; Langarudi, M. S. N.; Daneshvar, N.; Jamasbi, N.; Irankhah-Khanghah, M. Preparation and Characterization of [H2-DABCO][ClO4]2 as a New Member of DABCO-Based Ionic Liquids for the Synthesis of Pyrimido[4,5-b]-Quinoline and Pyrimido[4,5-d]Pyrimidine Derivatives. J. Mol. Struct. 2018, 1161, 366–382. DOI: 10.1016/j.molstruc.2018.02.069.
  • Bondle, G. M.; Atkore, S. T. Green Approach for Synthesizing Pyrimido Pyrimidine Moieties Using TBAB. J. Chem. Pharm. Res. 2016, 8, 717.
  • Kategaonkar, A. H.; Sadaphal, S. A.; Shelke, K. F.; Shingate, B. B.; Shingare, M. S. Microwave Assisted Synthesis of Pyrimido[4,5-d]Pyrimidine Derivatives in Dry Media. Ukr. Bioorg. Acta 2009, 3, 7.
  • Jadhav, C.; Khillare, L. D.; Bhosle, M. R. Efficient Sonochemical Protocol for the Facile Synthesis of Dipyrimido-Dihydropyridine and Pyrimido[4,5-d] Pyrimidines in Aqueous β-Cyclodextrin. Synth. Commun. 2018, 48, 233–246. DOI: 10.1080/00397911.2017.1390685.
  • Abdolmohammadi, S.; Afsharpour, M. An Operationally Simple Green Procedure for the Synthesis of Dihydropyrimido[4,5-d] Pyrimidinetriones Using CuI Nanoparticles as a Highly Efficient Catalyst. Z. Naturforsch. B 2015, 70, 171–176. DOI: 10.1515/znb-2014-0207.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.