Nanocrystalline titania-based sulfonic acid (TiO2-Pr-SO3H) as a new, highly efficient, and recyclable solid acid catalyst for preparation of quinoxaline derivatives
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Abstract
Nanocrystalline titania-based sulfonic acid (TiO 2 -Pr-SO 3 H) was used as an efficient and reusable catalyst for the synthesis of quinoxalines. The clean and mild acidity condition, quantitative yields of products, short reaction time, and low reaction temperature are attractive features of this method, making it suitable for heat- or acid-sensitive substrates, particularly in drug synthesis. In practice, this method affords an advantageous combination of satisfactory yields, easy product isolation, and purification.
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: Synthesis and Biological Evaluation · Quinazolinone synthesis and applications
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References (20)
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1. Sarges R, Howard HR, Browne RC, Label LA, Seymour PA: 4-Amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants. J Med Chem 1990, 33: 2240–2254. 10.1021/jm00170a03110.1021/jm00170a031 ↗
2. Brown KL: Chemistry and enzymology of vitamin B 12 . Chem Rev 2005, 105: 2075–2150. 10.1021/cr030720z10.1021/cr030720z ↗
3. Sakata G, Makino K, Kuraswa Y: Recent progress in the quinoline chemistry: synthesis and biological activity. Heterocycles 1998, 27: 2481–2515.
4. Ali MM, Ismail MMF, El-Gabby MSA, Zahran MA, Ammar TA: Synthesis and antimicrobial activities of some novel quinoxalinone derivatives. Molecules 2000, 5: 864–873. 10.3390/5060086410.3390/50600864 ↗
5. Sonawane ND, Rangnekar DW: Synthesis and application of 2-styryl-6,7-dichlorothiazolo[4,5- b ]-quinoxaline based fluorescent dyes: part 3. J Heterocycl Chem 2002, 39: 303–308. 10.1002/jhet.557039021010.1002/jhet.5570390210 ↗
6. Dailey S, Feast JW, Peace RJ, Sage IC, Till S, Wood EL: Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications. J Mater Chem 2001, 11: 2238–2243. 10.1039/b104674h10.1039/b104674h ↗
7. Elwahy AHM: Synthesis of new benzo-substituted macrocyclic ligands containing quinoxaline subunits. Tetrahedron 2000, 56: 897–907. 10.1016/S0040-4020(99)01072-810.1016/S0040-4020(99)01072-8 ↗
8. Crossley JC, Johnston LA: Laterally-extended porphyrin systems incorporating a switchable unit. Chem Commun 2002. 10.1039/B111655J
9. Jafarpour M, Rezaeifard A, Danehchin M: Easy access to quinoxaline derivatives using alumina as an effective and reusable catalyst under solvent-free conditions. Appl Catal A: Gen 2011, 394: 48–51. 10.1016/j.apcata.2010.12.02210.1016/j.apcata.2010.12.022 ↗
10. Huang TK, Wang R, Shi L, Lu X: Montmorillonite K-10: an efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water. Catal Commun 2008, 9: 1143–1147. 10.1016/j.catcom.2007.10.02410.1016/j.catcom.2007.10.024 ↗
11. Krishnakumar B, Swaminathan M: Solvent free synthesis of quinoxalines, dipyridophenazines and chalcones under microwave irradiation with sulfated Degussa titania as a novel solid acid catalyst. J Mol Catal A: Chem 2011, 350: 16–25. 10.1016/j.molcata.2011.08.02610.1016/j.molcata.2011.08.026 ↗
12. Krishnakumar B, Swaminathan M: A recyclable and highly effective sulfated TiO 2 -P25 for the synthesis of quinoxaline and dipyridophenazine derivatives at room temperature. J Organomet Chem 2010, 695: 2572–2577. 10.1016/j.jorganchem.2010.08.05510.1016/j.jorganchem.2010.08.055 ↗
13. Krishnakumar B, Velmurugan R, Jothivel S, Swaminathan M: An efficient protocol for the green synthesis of quinoxaline and dipyridophenazine derivatives at room temperature using sulfated titania. Catal Commun 2010, 11: 997–1002. 10.1016/j.catcom.2010.04.02110.1016/j.catcom.2010.04.021 ↗
14. Dhakshinamoorthy A, Kanagaraj K, Pitchumani K: Zn 2+ -K10-clay (clayzic) as an efficient water-tolerant, solid acid catalyst for the synthesis of benzimidazoles and quinoxalines at room temperature. Tetrahedron Lett 2011, 52: 69–73. 10.1016/j.tetlet.2010.10.14610.1016/j.tetlet.2010.10.146 ↗
15. Sharma RK, Sharma C: Zirconium(IV)-modified silica gel: preparation, characterization and catalytic activity in the synthesis of some biologically important molecules. Catal Commun 2011, 12: 327–331. 10.1016/j.catcom.2010.10.01110.1016/j.catcom.2010.10.011 ↗
16. Zhang XZ, Wang JX, Sun YJ, Zhan HW: Synthesis of quinoxaline derivatives catalyzed by PEG-400. Chin Chem Lett 2010, 21: 395–398. 10.1016/j.cclet.2009.12.01510.1016/j.cclet.2009.12.015 ↗
17. Heravi MM, Bakhtiari K, Bamoharram FF, Tehrani MH: Wells-Dawson type heteropolyacid catalyzed synthesis of quinoxaline derivatives at room temperature. Monatsh Chem 2007, 138: 465–467. 10.1007/s00706-007-0594-510.1007/s00706-007-0594-5 ↗
18. Ajaikumar S, Pandurangan A: Efficient synthesis of quinoxaline derivatives over ZrO 2 /M x O y (M = Al, Ga, In and La) mixed metal oxides supported on MCM-41 mesoporous molecular sieves. Appl Catal A Gen 2009, 357: 184–192. 10.1016/j.apcata.2009.01.02110.1016/j.apcata.2009.01.021 ↗
19. Shaabani A, Rezayan AH, Behnam M, Heidary M: Green chemistry approaches for the synthesis of quinoxaline derivatives: comparison of ethanol and water in the presence of the reusable catalyst cellulose sulfuric acid. C R Chimie 2009, 12: 1249–1252. 10.1016/j.crci.2009.01.00610.1016/j.crci.2009.01.006 ↗
20. Cai JJ, Zou JP, Pan XQ, Zhang W: Gallium(III) triflate-catalyzed synthesis of quinoxaline derivatives. Tetrahedron Lett 2008, 49: 7386–7390. 10.1016/j.tetlet.2008.10.05810.1016/j.tetlet.2008.10.058 ↗