Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Latest Articles
28
Views
0
CrossRef citations to date
0
Altmetric
Review Article

An overall development on catalytic applications of potassium phthalimide (PPI) and potassium phthalimide-N-oxyl (POPINO) in organic synthesis

, , ORCID Icon &
Received 11 Feb 2024, Published online: 25 Apr 2024

References

  • Aukland, M. H.; List, B. Organocatalysis Emerging as a Technology. Pure Appl. Chem. 2021, 93, 1371–1381. DOI: 10.1515/pac-2021-0501.
  • Parvin, T.; Yadav, R.; Choudhury, L. H. Recent Applications of Thiourea-Based Organocatalysts in Asymmetric Multicomponent Reactions (AMCRs). Org. Biomol. Chem. 2020, 18, 5513–5532. DOI: 10.1039/d0ob00595a.
  • Ganesh, M.; Ramakrishna, J. Synthetic Organic Transformations of Transition-Metal Nanoparticles as Propitious Catalysts: A Review. Asian J. Org. Chem. 2020, 9, 1341–1376. DOI: 10.1002/ajoc.202000379.
  • Arora, A.; Oswal, P.; Rao, G. K.; Kumar, S.; Kumar, A. Organoselenium Ligands for Heterogeneous and Nanocatalytic Systems: development and Applications. Dalton Trans. 2021, 50, 8628–8656. DOI: 10.1039/d1dt00082a.
  • Vekariya, R. H.; Patel, H. D. Sulfonated Polyethylene Glycol (PEG-OSO3H) as a Polymer Supported Biodegradable and Recyclable Catalyst in Green Organic Synthesis: recent Advances. RSC Adv. 2015, 5, 49006–49030. DOI: 10.1039/C5RA06532A.
  • Swami, S.; Sahu, S. N.; Shrivastava, R. Nanomaterial Catalyzed Green Synthesis of Tetrazoles and Its Derivatives: A Review on Recent Advancements. RSC Adv. 2021, 11, 39058–39086. DOI: 10.1039/d1ra05955f.
  • Vekariya, R. H.; Patel, K. D.; Patel, H. D. A Green and One-Pot Synthesis of a Library of 1,4-Dihydropyrano[2,3-c]-Pyrazole-5-Carbonitrile Derivatives Using Thiourea Dioxide (TUD) as an Efficient and Reusable Organocatalyst. Res. Chem. Intermed. 2016, 42, 4683–4696. DOI: 10.1007/s11164-015-2308-7.
  • Sheehan, J. C.; Bolhofer, W. A. An Improved Procedure for the Condensation of Potassium Phthalimide with Organic Halides. J. Am. Chem. Soc. 1950, 72, 2786–2788. DOI: 10.1021/ja01162a527.
  • Climent, M. J.; Corma, A.; Iborra, S. Homogeneous and Heterogeneous Catalysts for Multicomponent Reactions. RSC Adv. 2012, 2, 16–58. DOI: 10.1039/C1RA00807B.
  • Ragnarsson, U.; Grehn, L. Novel Gabriel Reagents. Acc. Chem. Res. 1991, 24, 285–289. DOI: 10.1021/ar00010a001.
  • Sorokin, A. B. Phthalocyanine Metal Complexes in Catalysis. Chem. Rev. 2013, 113, 8152–8191. DOI: 10.1021/cr4000072.
  • Debecker, D. P.; Gaigneaux, E. M.; Busca, G. Exploring, Tuning, and Exploiting the Basicity of Hydrotalcites for Applications in Heterogeneous Catalysis. Chemistry 2009, 15, 3920–3935. DOI: 10.1002/chem.200900060.
  • H Vekariya, R.; D Patel, K.; P Prajapati, N.; D Patel, H. Potassium Phthalimide (PPI): an Efficient and Green Organocatalyst for the One-Pot Synthesis of 6-Amino-1,4-Dihydropyrano [2, 3-c]-Pyrazole-5-Carbonitrile Derivatives under Microwave Irradiation. CMIC 2017, 4, 122–127. DOI: 10.2174/2213335603666160408162601.
  • Kiyani, H.; Ghorbani, F. Potassium Phthalimide Promoted Green Multicomponent Tandem Synthesis of 2-Amino-4H-Chromenes and 6-Amino-4H-Pyran-3-Carboxylates. J. Saudi Chem. Soc. 2014, 18, 689–701. DOI: 10.1016/j.jscs.2014.02.004.
  • Smith, M. B. March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure; John Wiley & Sons: New York, 2020.
  • Charette, A. B. Handbook of Reagents for Organic Synthesis: Reagents for Heteroarene Functionalization; John Wiley & Sons: New York, 2015.
  • Chung, S.-H.; Lin, T.-J.; Hu, Q.-Y.; Tsai, C.-H.; Pan, P.-S. Synthesis of Boron-Containing Primary Amines. Molecules 2013, 18, 12346–12367. DOI: 10.3390/molecules181012346.
  • Mitsunobu, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products. Synthesis 1981, 1981, 1–28. DOI: 10.1055/s-1981-29317.
  • Ghorbani, F.; Kiyani, H. Facile Three-Component Synthesis of 7-Arylbenzo[f]Chromeno[4,3-b] Chromen-6(7H)-Ones Catalyzed by Potassium Phthalimide in Aqueous Media. JJC 2014, 9, 1–6. DOI: 10.12816/0026390.
  • Kiyani, H.; Ghiasi, M. Potassium Phthalimide: An Efficient and Green Organocatalyst for the Synthesis of 4-Aryl-7-(Arylmethylene)-3,4,6,7-Tetrahydro-1H-Cyclopenta [d] Pyrimidin-2 (5H)-Ones/Thiones under Solvent-Free Conditions. Chin. Chem. Lett. 2014, 25, 313–316. DOI: 10.1016/j.cclet.2013.11.042.
  • Kiyani, H.; Ghorbani, F. Potassium Phthalimide as Efficient Basic Organocatalyst for the Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-Ones in Aqueous Medium. J. Saudi Chem. Soc. 2017, 21, S112–S119. DOI: 10.1016/j.jscs.2013.11.002.
  • Kiyani, H.; Ghorbani, F. Potassium Phthalimide: An Efficient and Simple Organocatalyst for the One-Pot Synthesis of Dihydropyrano[3,2-c]Chromenes in Aqueous Media. Res. Chem. Intermed. 2015, 41, 4031–4046. DOI: 10.1007/s11164-013-1508-2.
  • Kiyani, H.; Ghorbani, F. Potassium Phthalimide-Catalysed One-Pot Multi-Component Reaction for Efficient Synthesis of Amino-Benzochromenes in Aqueous Media. Chem. Pap. 2014, 68, 1104–1112.
  • Kiyani, H.; Ghiasi, M. Solvent-Free Efficient One-Pot Synthesis of Biginelli and Hantzsch Compounds Catalyzed by Potassium Phthalimide as a Green and Reusable Organocatalyst. Res. Chem. Intermed. 2015, 41, 5177–5203. DOI: 10.1007/s11164-014-1621-x.
  • Odiya, S.; Das, S.; Boruah, J.; Rajani, D. Synthesis of New Cyclohexenone Derivatives Using Potassium Phthalimide as a Green Organocatalyst. one-Pot Microwave-Assisted Synthesis and Antimicrobial Evaluation. Russ. J. Org. Chem. 2023, 59, 117–132. DOI: 10.1134/S107042802301013X.
  • Odiya, S. P.; Das, S. P.; Boruah, J. J.; Rajani, D. P. R. D. P. Microwave-Assisted Synthesis of-CF3 Functionalized 3,4-Dihydropyrimidinone/Thione/Imine Derivatives by Using Potassium Phthalimide (PPI) as a Green and Reusable Organocatalyst and Their anti-Microbial Evaluation. Ind. J. Chem. 2023, 62, 600–617.
  • Kiyani, H.; Daroonkala, M. D. A Cost-Effective and Green Aqueous Synthesis of 3-Substituted Coumarins Catalyzed by Potassium Phthalimide. Bull. Chem. Soc. Eth. 2015, 29, 449–456. DOI: 10.4314/bcse.v29i3.13.
  • Kiyani, H.; Bamdad, M. One-Pot Four-Component Synthesis of 1,4-Dihydropyrano[2,3-c]Pyrazole-5-Carbonitriles Catalyzed by Potassium Phthalimide. Rev. Roum. Chim. 2017, 62, 221–226.
  • Yu, X.; Zhou, Z. Potassium Phthalimide Catalyzed Efficient Synthesis of 2-Amino-3-Phenylsulfonyl-4H-Chromenes under solvent-Free Conditions. Phosphorus Sulfur Silicon Relat. Elem. 2018, 193, 387–393. DOI: 10.1080/10426507.2018.1424161.
  • Moghaddam, F. M.; Dekamin, M. G.; Koozehgari, G. R. A Simple and Efficient Method for Synthesis of Isocyanurates Catalyzed by Potassium Phthalimide under Solvent-Free Conditions. LOC 2005, 2, 734–738. DOI: 10.2174/157017805774717508.
  • Dekamin, M. G.; Karimi, Z. Activation of Trimethylsilyl Cyanide by Potassium Phthalimide for Facile Synthesis of TMS-Protected Cyanohydrins. J. Organomet. Chem. 2009, 694, 1789–1794. DOI: 10.1016/j.jorganchem.2009.01.058.
  • Dekamin, M. G.; Javanshir, S.; Naimi-Jamal, M. R.; Hekmatshoar, R.; Mokhtari, J. Potassium phthalimide-N-Oxyl: An Efficient Catalyst for Cyanosilylation of Carbonyl Compounds under Mild Conditions. J. Mol. Catal. A Chem. 2008, 283, 29–32. DOI: 10.1016/j.molcata.2007.12.007.
  • Dekamin, M. G.; Peyman, S. Z. Phthalimide-N-Oxyl Salts: efficient Organocatalysts for Facile Synthesis of (Z)-3-Methyl-4-(Arylmethylene)-Isoxazole-5(4H)-One Derivatives in Water. Monatsh. Chem. 2016, 147, 445–450. DOI: 10.1007/s00706-015-1565-x.
  • Dekamin, M. G.; Eslami, M.; Maleki, A. Potassium Phthalimide-N-Oxyl: A Novel, Efficient, and Simple Organocatalyst for the One-Pot Three-Component Synthesis of Various 2-Amino-4H-Chromene Derivatives in Water. Tetrahedron 2013, 69, 1074–1085. DOI: 10.1016/j.tet.2012.11.068.
  • Etivand, N.; Khalafy, J.; Dekamin, M. G. Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]Chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium phthalimide-N-Oxyl. Synthesis 2020, 52, 1707–1718. DOI: 10.1055/s-0037-1610755.

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.