Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 16
161
Views
5
CrossRef citations to date
0
Altmetric
Articles

An efficient and green protocol for synthesis of novel [1,3]oxazino[5,6-c]quinolin-5-one derivatives using [Et3NH]HSO4 as a reusable catalyst

&
Pages 2044-2052 | Received 23 Oct 2018, Published online: 16 May 2019

References

  • Michael, J. P. Quinoline, Quinazoline and Acridone Alkaloids. Nat. Prod. Rep. 2008, 25, 166–187. DOI: 10.1039/B612168N.
  • Arya, K.; Agarwal, M. Microwave Prompted Multigram Synthesis, Structural Determination, and Photo-Antiproliferative Activity of Fluorinated 4-Hydroxyquinolinones. Bioorg. Med. Chem. Lett. 2007, 17, 86–93. DOI: 10.1016/j.bmcl.2006.09.082.
  • Oeveren, A.; Motamedi, M.; Martinborough, E.; Zhao, S.; Shen, Y.; West, S.; Chang, W.; Kallel, A.; Marschke, K. B.; Lopez, F. J.; et al. Novel Selective Androgen Receptor Modulators: SAR Studies on 6-Bisalkylamino-2-Quinolinones. Bioorg. Med. Chem. Lett. 2007, 17, 1527–1531. DOI: 10.1016/j.bmcl.2007.01.001.
  • Baruah, B.; Dasu, K.; Vaitilingam, B.; Vanguri, A.; Casturi, S. R.; Yeleswarapu, K. R. 1,2-Diaryl-1-Ethanone and Pyrazolo [4,3-C] Quinoline-4-One as Novel Selective Cyclooxygenase-2 Inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 445–448. DOI: 10.1016/j.bmcl.2003.10.052.
  • Ahmed, N.; Brahmbhatt, K. G.; Sabde, S.; Mitra, D.; Singh, I. P.; Bhutani, K. K. Synthesis and anti-HIV Activity of Alkylated Quinoline 2,4-Diols. Bioorg. Med. Chem. 2010, 18, 2872–2879. DOI: 10.1016/j.bmc.2010.03.015.
  • Ismaili, L.; Nadaradjane, A.; Nicod, L.; Guyon, C.; Xicluna, A.; Robert, J.; Refouvelet, B. Synthesis and Antioxidant Activity Evaluation of New Hexahydropyrimido[5, -C]Quinoline-2,5-Diones and 2-Thioxohexahydropyrimido[5,4-C]Quinoline-5-Ones Obtained by Biginelli Reaction in Two Steps. Eur. J. Med. Chem. 2008, 43, 1270–1275. DOI: 10.1016/j.ejmech.2007.07.012.
  • Cheng, P.; Gu, Q.; Liu, W.; Zou, J.; Ou, Y.; Luo, Z.; Zeng, J. Synthesis of Quinolin-2-One Alkaloid Derivatives and Their Inhibitory Activities against HIV-1 Reverse Transcriptase. Molecules 2011, 16, 7649–7661. DOI: 10.3390/molecules16097649.
  • Hamama, W. S.; Hassanien, A. E. E.; Zoorob, H. H. Studies on Quinolinedione: Synthesis, Reactions, and Applications. Synth. Commun. 2014, 44, 1833–1858. DOI: 10.1080/00397911.2013.867352.
  • Watpade, R.; Bholay, A.; Toche, R. J. Synthesis of New Pyrano-Fused Quinolines as Antibacterial and Antimicrobial Agents. J. Heterocyclic Chem. 2017, 54, 3434–3439. DOI: 10.1002/jhet.2966.
  • Khalafy, J.; Arlan, F. M.; Chalanchi, S. S. One-Pot, Three-Component Synthesis of a New Series of 2-Amino-4-Aroyl-5-Oxo-5,6-Dihydro-2H-Pyrano[3,2-c]Quinoline-3-Carbonitrile in the Presence of SBA-15 as a Nanocatalyst. J. Heterocyclic Chem. 2018, 55, 149–153. DOI: 10.1002/jhet.3017.
  • Adib, M.; Sheibani, E.; Mostofi, M.; Ghanbary, K.; Bijanzadeh, H. R. Efficient Highly Diastereoselective Synthesis of 1,8a-Dihydro-7H-Imidazo[2,1-b][1,3]Oxazines. Tetrahedron 2006, 62, 3435–3438. DOI: 10.1016/j.tet.2006.01.048.
  • Kurz, T. Synthesis of Novel Pyrido[2,3-e][1,3]Oxazines. Tetrahedron 2005, 61, 3091–3096. DOI: 10.1016/j.tet.2005.01.039.
  • Zhang, P.; Terefenko, E. A.; Fensome, A.; Wrobel, J.; Winneker, R.; Zhang, Z. Novel 6-Aryl-1,4-Dihydrobenzo[d][1,3]Oxazine-2-Thiones as Potent, Selective, and Orally Active Nonsteroidal Progesterone Receptor Agonists. Bioorg. Med. Chem. Lett. 2003, 13, 1313–1316. DOI: 10.1016/S0960-894X(03)00128-8.
  • Poel, H. V.; Guilaumet, G.; Viaud-Massuard, M. Synthesis of 6,7,8,9-Tetrahydropyrido[2, 3-b]Indolizine and 3,4-Dihydro-2H-Pyrido[2′,3′:4,5]pyrrolo[2,1-b][1,3]oxazine Derivatives as New Melatonin Receptor Ligands. Tetrahedron Lett. 2002, 43, 1205–1208. DOI: 10.1016/S0040-4039(01)02359-0.
  • Zanatta, N.; Squizani, A. M. C.; Fantinel, L.; Nachtigall, F. M.; Borchhardt, D. M.; Bonacorso, H. G.; Martins, M. A. P. Synthesis of N-Substituted 6-Trifluoromethyl-1,3-Oxazinanes. J. Braz. Chem. Soc. 2005, 16, 1255–1261. DOI: 10.1590/S0103-50532005000700025.
  • Dömling, A.; Wang, W.; Wang, K. Chemistry and Biology of Multicomponent Reactions. Chem. Rev. 2012, 112, 3083–3135. DOI: 10.1021/cr100233r.
  • Brauch, S.; Berkel, S. S.; Westermann, B. Higher-Order Multicomponent Reactions: Beyond Four Reactants. Chem. Soc. Rev. 2013, 42, 4948–4962. DOI: 10.1039/c3cs35505e.
  • Cioc, R. C.; Ruijter, E.; Orru, R. V. A. Multicomponent Reactions: Advanced Tools for Sustainable Organic Synthesis. Green Chem. 2014, 16, 2958–2975. DOI: 10.1039/C4GC00013G.
  • Singh, M. S.; Chowdhury, S. Recent Developments in Solvent-Free Multicomponent Reactions: A Perfect Synergy for Eco-Compatible Organic Synthesis. RSC Adv. 2012, 2, 4547–4592. DOI: 10.1039/c2ra01056a.
  • Biggs-Houck, J. E.; Younai, A.; Shaw, J. T. Recent Advances in Multicomponent Reactions for Diversity-Oriented Synthesis. Curr. Opin. Chem. Biol. 2010, 14, 371–382. DOI: 10.1016/j.cbpa.2010.03.003.
  • Hajipour, A. R.; Rafiee, F. Acidic Bronsted Ionic Liquids. Org. Prep. Proced. Int. 2010, 42, 285–362. DOI: 10.1080/00304948.2010.490177.
  • Wang, C.; Guo, L.; Li, H.; Wang, Y.; Weng, J.; Wu, L. Preparation of Simple Ammonium Ionic Liquids and Their Application in the Cracking of Dialkoxypropanes. Green Chem. 2006, 8, 603–607. DOI: 10.1039/b600041j.
  • Patil, S. K.; Awale, D. V.; Vadiyar, M. M.; Patil, S. A.; Bhise, S. C.; Kolekar, S. S. Simple Protic Ionic Liquid [Et3NH][HSO4] as a Proficient Catalyst for Facile Synthesis of Biscoumarins. Res. Chem. Intermed. 2017, 43, 5365–5376. DOI: 10.1007/s11164-017-2932-5.
  • Zhou, Z.; Deng, X. [Et3NH][HSO4] Catalyzed Efficient and Green Synthesis of 1,8-Dioxo-Octahydroxanthenes. J. Mol. Catal. A: Chem. 2013, 367, 99–102. DOI: 10.1016/j.molcata.2012.11.002.
  • Tanaka, K.; Toda, F. Solvent-Free Organic Synthesis. Chem. Rev. 2000, 100, 1025–1074. DOI: 10.1021/cr940089p.
  • Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Buriol, L.; Machado, P. Solvent-Free Heterocyclic Synthesis. Chem. Rev. 2009, 109, 4140–4182. DOI: 10.1021/cr9001098.
  • Li, C. J.; Chen, L. Organic Chemistry in Water. Chem. Soc. Rev. 2006, 35, 68–82. DOI: 10.1039/B507207G.
  • Chanda, A.; Fokin, V. V. Organic Synthesis “on Water”. Chem. Rev. 2009, 109, 725–748. DOI: 10.1021/cr800448q.
  • Chandrasekhar, S.; Patro, V.; Reddy, G. P. K.; Gree, R. A Ligand-Free Copper(II)-Catalyzed Three-Component Reaction in Poly(Ethylene Glycol) Medium: A Versatile Protocol for the Preparation of Selected 3-Indole Derivatives. Tetrahedron Lett. 2012, 53, 6223–6225. DOI: 10.1016/j.tetlet.2012.09.008.
  • Brahmachari, G.; Banerjee, B. Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-Cyano-4H-Pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst. ACS Sustainable Chem. Eng. 2014, 2, 411–422. DOI: 10.1021/sc400312n.
  • Kumar, P. S. V.; Suresh, L.; Bhargavi, G.; Basavoju, S.; Chandramouli, G. V. P. Ionic Liquid-Promoted Green Protocol for the Synthesis of Novel Naphthalimide-Based Acridine-1,8-Dione Derivatives via a Multicomponent Approach. ACS Sustainable Chem. Eng. 2015, 3, 2944–2950. DOI: 10.1021/acssuschemeng.5b00900.
  • Kong, D.; Lu, G.; Wu, M.; Shi, Z.; Lin, Q. One-Pot, Catalyst-Free Synthesis of Spiro[Dihydroquinolinenaphthofuranone] Compounds from Isatins in Water Triggered by Hydrogen Bonding Effects. ACS Sustainable Chem. Eng. 2017, 5, 3465–3470. DOI: 10.1021/acssuschemeng.7b00145.

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.