Reduced graphene oxide/NiO nanocomposites as a highly effective, efficient, and recyclable heterogeneous catalyst towards one pot of synthesis of 2-arylbenzoxazoles/thiazoles
Bibliographic record
Abstract
No abstract is available for this record. The assistant can identify its topic from the title, but cannot infer the study’s results.
Source: Not provided · Quality: missing
Research context
OpenAlex topics: Multicomponent Synthesis of Heterocycles · Chemical Synthesis and Reactions · Microwave-Assisted Synthesis and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (63)
Show source-provided references
1. B. Maleki, H. Salehabadi, Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives. Eur. J. Chem. 1(4), 377–380 (2010). https://doi.org/10.5155/eurjchem.1.4.377-380.16510.5155/eurjchem.1.4.377-380.165 ↗
2. T.D. Bradshaw, A.D. Westwell, The development of the antitumour benzothiazole prodrug, phortress, as a clinical candidate. Curr. Med. Chem. 11(8), 1009–1021 (2005). https://doi.org/10.2174/092986704345553010.2174/0929867043455530 ↗
3. S.J. Hays, M.J. Rice, D.F. Ortwine, G. Johnson, R.D. Schwarz, D.K. Boyd, L.F. Copeland, M.G. Vartanian, P.A. Boxer, Substituted 2-benzothiazolamines as sodium flux inhibitors: Quantitative structure-activity relationships and anticonvulsant activity. J. Pharm. Sci. 83(10), 1425–1432 (1994). https://doi.org/10.1002/JPS.260083101310.1002/JPS.2600831013 ↗
4. D. Russell, G. Viirre; Evindar, R.A. Batey, Nocopper-catalyzed domino annulation approaches to the synthesis of benzoxazoles under microwave-accelerated and conventional thermal conditions. J. Org. Chem. 73(9), 3452–3459 (2008). https://doi.org/10.1021/jo702145d10.1021/jo702145d ↗
5. M. Taki, J.L. Wolford, T.V. O’Halloran, Emission ratiometric imaging of intracellular zinc: Design of a benzoxazole fluorescent sensor and its application in two-photon microscopy. J. Am. Chem. Soc. 126(3), 712–713 (2004). https://doi.org/10.1021/JA039073J10.1021/JA039073J ↗
6. C.J. Paget, R.L. Stone, K. Kisner, D.C. DeLong, Heterocyclic substituted ureas. II. immunosuppressive and antiviral activity of benzothiazole- and benzoxazoleureas. J. Med. Chem. 12(6), 1016–1018 (1969). https://doi.org/10.1021/JM00306A011/ASSET/JM00306A011.FP.PNG_V0310.1021/JM00306A011/ASSET/JM00306A011.FP.PNG_V03 ↗
7. S.R. Mathapati, K.N. Patil, S. Sujit, A.W. Mathakari, S. Jadhav, Fluorinated phosphoric acid as a versatile effective catalyst for synthesis of series of benzimidazoles, benzoxazoles and benzothiazoles at room temperature. Phosphorus Sulfur Silicon Relat. Elem. 196(6), 538–547 (2021). https://doi.org/10.1080/10426507.2020.187134510.1080/10426507.2020.1871345 ↗
8. S. Samanta, S. Das, P. Biswas, Photocatalysis by 3,6-disubstituted-s-tetrazine: visible-light driven metal-free green synthesis of 2-substituted benzimidazole and benzothiazole. J. Org. Chem. 78(22), 11184–11193 (2013). https://doi.org/10.1021/JO401445J/SUPPL_FILE/JO401445J_SI_001.PDF10.1021/JO401445J/SUPPL_FILE/JO401445J_SI_001.PDF ↗
9. X. Wen, J.E. Bakali, R. Deprez-Poulain, B. Deprez, Efficient propylphosphonic anhydride (®T3P) mediated synthesis of benzothiazoles, benzoxazoles and benzimidazoles. Tetrahedron Lett. 53(19), 2440–2443 (2012). https://doi.org/10.1016/J.TETLET.2012.03.00710.1016/J.TETLET.2012.03.007 ↗
10. N.S. Kozlov, B.I. Kiselev, Catalytic synthesis of 2-alkylbenzoxazoles. Chem. Heterocycl. Compd. 2(3), 248–249 (1967). https://doi.org/10.1007/BF00742357/METRICS10.1007/BF00742357/METRICS ↗
11. R.S. Pottorf, K. Naresh, M.K. Chadha, V. Ozola, E. Suna, B.H. Ghane, T.R. And, M.R. Player, Parallel synthesis of benzoxazoles via microwave-assisted dielectric heating. Tetrahedron Lett. 44, 175–178 (2003)10.1016/S0040-4039(02)02495-4 ↗
12. Y. Sun, H. Jiang, W. Wu, W. Zeng, X. Wu, Copper-catalyzed synthesis of substituted benzothiazoles via condensation of 2-aminobenzenethiols with nitriles. Org. Lett. 15(7), 1598–1601 (2013). https://doi.org/10.1021/OL400379Z/SUPPL_FILE/OL400379Z_SI_001.PDF10.1021/OL400379Z/SUPPL_FILE/OL400379Z_SI_001.PDF ↗
13. H. Matsushita, S.-H. Lee, M. Joung, B. Clapham, K.D. Janda, Smart cleavage reactions: the synthesis of benzimidazoles and benzothiazoles from polymer. Tetrahedron Lett. (2004) https://doi.org/10.1016/j.tetlet.2003.10.16810.1016/j.tetlet.2003.10.168 ↗
14. C. Praveen, K.H. Kumar, D. Muralidharan, P.T. Perumal, Oxidative cyclization of thiophenolic and phenolic schiff’s bases promoted by pcc: A new oxidant for 2-substituted benzothiazoles and benzoxazoles. Tetrahedron 64, 2369–2374 (2008)10.1016/j.tet.2008.01.004 ↗
15. R.G. Srivastava, P.S. Venkataramani, Barium manganate oxidation in organic synthesis: part III: oxidation of Schiff’s bases to benzimidazoles benzoxazoles and benzthiazoles. Synth. Commun. 18, 1537–1544 (1988)10.1080/00397918808081311 ↗
16. S.K. Sahoo, N. Khatun, A. Gogoi, A. Deb, B.K. Patel, Cu(II) catalysed chemoselective oxidative transformation of thiourea to thioamidoguanidine/2-aminobenzothiazole. RSC Adv. 3(2), 438–446 (2012). https://doi.org/10.1039/C2RA22240J10.1039/C2RA22240J ↗
17. K. Liu, F. Jia, H. Xi, Y. Li, X. Zheng, Q. Guo, B. Shen, Z. Li, Direct benzothiophene formation via oxygen-triggered intermolecular cyclization of thiophenols and alkynes assisted by manganese/PhCOOH. Org. Lett. 15(8), 2026–2029 (2013). https://doi.org/10.1021/OL400719D/SUPPL_FILE/OL400719D_SI_001.PDF10.1021/OL400719D/SUPPL_FILE/OL400719D_SI_001.PDF ↗
18. T. Itoh, T.A. Mase, Novel practical synthesis of benzothiazoles via Pd-catalyzed thiol cross-coupling. Org. Lett. 9(18), 3687–3689 (2007). https://doi.org/10.1021/OL7015737/SUPPL_FILE/OL7015737.DOC10.1021/OL7015737/SUPPL_FILE/OL7015737.DOC ↗
19. G. Evindar, R.A. Batey, Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides. J. Org. Chem. 71(5), 1802–1808 (2006). https://doi.org/10.1021/JO051927Q/SUPPL_FILE/JO051927QSI20051203_122427.PDF10.1021/JO051927Q/SUPPL_FILE/JO051927QSI20051203_122427.PDF ↗
20. R.S. Varma, R.K. Saini, O. Prakash, Hypervalent iodine oxidation of phenolic Schiff’s bases: synthesis of 2-arylbenzoxazoles. Tetrahedron Lett. 38(15), 2621–2622 (1997). https://doi.org/10.1016/S0040-4039(97)00444-910.1016/S0040-4039(97)00444-9 ↗
21. R.S. Varma, D. Kumar, Manganese triacetate oxidation of phenolic Schiffs bases: synthesis of 2-arylbenzoxazoles. J. Heterocycl. Chem. 35(6), 1539–1540 (1998). https://doi.org/10.1002/JHET.557035065610.1002/JHET.5570350656 ↗
22. K.H. Park, K. Jun, S.R. Shin, S.W. Oh, 2-arylbenzoxazoles from phenolic Schiff’s bases by thianthrene cation radical. Tetrahedron Lett. 37(49), 8869–8870 (1996). https://doi.org/10.1016/S0040-4039(96)02070-910.1016/S0040-4039(96)02070-9 ↗
23. K. Nakagawa, H. Onoue, J. Sugita, Oxidation with nickel peroxide. IV. The preparation of benzoxazoles from Schiff’s bases. Chem. Pharm. Bull. Tokyo 12(10), 1135–1138 (1964). https://doi.org/10.1248/cpb.12.113510.1248/cpb.12.1135 ↗
24. J.J. Vanden Eynde, F. Delfosse, P. Lor, Y. Van Haverbeke, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, a mild catalyst for the formation of carbon-nitrogen bonds. Tetrahedron 51(20), 5813–5818 (1995). https://doi.org/10.1016/0040-4020(95)00252-410.1016/0040-4020(95)00252-4 ↗
25. K. Bahrami, M. Mehdi Khodaei, F. Naali, Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles. J. Org. Chem. 73(17), 6835–6837 (2008). https://doi.org/10.1021/JO801023210.1021/JO8010232 ↗
26. V.I. Cohen, A new method of synthesis of some 2-aryl and 2‐heterocyclic benzimidazole, benzoxazole and benzothiazole derivatives. J. Heterocycl. Chem. 16(1), 13–16 (1979). https://doi.org/10.1002/JHET.557016010310.1002/JHET.5570160103 ↗
27. S. Abdolmohammadi, ZnO nanoparticles-catalyzed cyclocondensation reaction of arylmethylidenepyruvic acids with 6-aminouracils. Comb. Chem. High. Throughput Screen. 16(1), 32–36 (2013). https://doi.org/10.2174/138620731131601000510.2174/1386207311316010005 ↗
28. S. Abdolmohammadi, Solvent-free synthesis of 4,5-dihydropyrano[c]chromene derivatives over TiO2 nanoparticles as an economical and efficient catalyst. Curr. Catal. 2(2), 116–121 (2013). https://doi.org/10.2174/221154471130202000510.2174/2211544711302020005 ↗
29. S. Abdolmohammadi, M. Afsharpour, S. Keshavarz-Fatideh, An efficient green synthesis of 3-amino-1H-chromenes catalyzed by ZnO nanoparticles thin-film. South. Afr. J. Chem. 67(ii), 203–210 (2014)
30. S. Abdolmohammadi, Z. Aghaei-Meybodi, Simple and efficient route toward ambient preparation of pyrimido[b]quinolinetriones using copper (I) iodide nanoparticles in aqueous media. Comb. Chem. High. Throughput Screen. 18(9), 911–916 (2015). https://doi.org/10.2174/138620731866615052509423410.2174/1386207318666150525094234 ↗
31. S. Abdolmohammadi, S.R. Rasouli Nasrabadi, M.R. Dabiri, S.M. Banihashemi Jozdani, TiO2 nanoparticles immobilized on carbon nanotubes: an efficient heterogeneous catalyst in cyclocondensation reaction of isatins with malononitrile and 4-hydroxycoumarin or 3,4-methylenedioxyphenol under mild reaction conditions. Appl. Organomet. Chem. (2020). https://doi.org/10.1002/aoc.546210.1002/aoc.5462 ↗
32. S. Abdolmohammadi, S. Shariati, B. Mirza, Ultrasound promoted and kit-6 mesoporous silica-supported Fe3O4 magnetic nanoparticles catalyzed cyclocondensation reaction of 4-hydroxycoumarin, 3,4-methylenedioxyphenol, and aromatic aldehydes. Appl. Organomet. Chem. 35(3), 1–10 (2021). https://doi.org/10.1002/aoc.611710.1002/aoc.6117 ↗
33. S. Banerjee, S. Payra, A. Saha, G. Sereda, ZnO nanoparticles: A green efficient catalyst for the room temperature synthesis of biologically active 2-aryl-1,3-benzothiazole and 1,3-benzoxazole derivatives. Tetrahedron Lett. 55(40), 5515–5520 (2014). https://doi.org/10.1016/j.tetlet.2014.07.12310.1016/j.tetlet.2014.07.123 ↗
34. S. Banerjee, Efficient room temperature synthesis of 2-aryl benzimidazoles using zno nanoparticles as reusable catalyst. Org. Med. Chem. Int. J. 1(4), 1–6 (2017). https://doi.org/10.19080/omcij.2017.01.55556810.19080/omcij.2017.01.555568 ↗
35. S. Banerjee, S. Payra, A.A. Saha, Review on synthesis of benzothiazole derivatives. Curr. Organocatal. 4(3), 164–181 (2018). https://doi.org/10.2174/221333720566618011914353910.2174/2213337205666180119143539 ↗
36. D.R. Dreyer, H.P. Jia, C.W. Bielawski, Graphene oxide: a convenient carbocatalyst for facilitating oxidation and hydration reactions. Angew Chemie Int. Ed. 49(38), 6813–6816 (2010). https://doi.org/10.1002/ANIE.20100216010.1002/ANIE.201002160 ↗
37. K.B. Dhopte, D.S. Raut, A.V. Patwardhan, P.R. Nemade, Graphene oxide as recyclable catalyst for one-pot synthesis of α-aminophosphonates. Synth. Commun. 45(6), 778–788 (2015). https://doi.org/10.1080/00397911.2014.989447/SUPPL_FILE/LSYC_A_989447_SM1669.PDF10.1080/00397911.2014.989447/SUPPL_FILE/LSYC_A_989447_SM1669.PDF ↗
38. M. Mirza-Aghayan, M. Alizadeh, M. Molaee Tavana, R. Boukherroub, Graphite oxide: A simple and efficient solid acid catalyst for the ring-opening of epoxides by alcohols. Tetrahedron Lett. 55, 6694–6697 (2014). https://doi.org/10.1016/j.tetlet.2014.10.05010.1016/j.tetlet.2014.10.050 ↗
39. K.B. Dhopte, R.S. Zambare, A.V. Patwardhan, P.R. Nemade, Role of graphene oxide as heterogeneous acid catalyst and benign oxidant for synthesis of benzimidazoles and benzothiazole. RSC Adv. 6, 8164–8172 (2016)10.1039/C5RA19066E ↗
40. M. Afsharpour, Z. Dini, One-pot functionalization of carbon nanotubes by WO3/MoO3 nanoparticles as oxidative desulfurization catalysts. Fullerenes Nanotub Carbon Nanostruct. 27(3), 198–205 (2019). https://doi.org/10.1080/1536383X.2018.153813210.1080/1536383X.2018.1538132 ↗
41. M. Afsharpour, E. Khomand, Synthesis of bio-inspired porous silicon carbides using Cortaderia selloana and Equisetum arvense grasses as remarkable sulfur adsorbents. Int. J. Environ. Sci. Technol. 16(7), 3125–3134 (2019). https://doi.org/10.1007/s13762-018-1679-x10.1007/s13762-018-1679-x ↗
42. N.S. Mehr, S. Abdolmohammadi, M. Afsharpour, Activated carbon/MoO3: Efficient catalyst for green synthesis of chromeno[d]pyrimidinediones and xanthenones. Comb. Chem. High. Throughput Screen. 24(5), 683–694 (2020). https://doi.org/10.2174/138620732366620092411160210.2174/1386207323666200924111602 ↗
43. S. Abdolmohammadi, M. Afsharpour, An ultrasound assisted cyclocondensation reaction for the efficient synthesis of [1]benzopyranopyrido[d]pyrimidines using porous graphene/MoO3. Appl. Organomet. Chem. (2021). https://doi.org/10.1002/aoc.602810.1002/aoc.6028 ↗
44. C. Su, K.P. Loh, Carbocatalysts: Graphene oxide and its derivatives. Acc. Chem. Res. 46(10), 2275–2285 (2013). https://doi.org/10.1021/ar300118v10.1021/ar300118v ↗
45. L. Sun, H. Yu, B. Fugetsu, Graphene oxide adsorption enhanced by in situ reduction with sodium hydrosulfite to remove acridine orange from aqueous solution. J. Hazard. Mater. 203–204, 101–110 (2012). https://doi.org/10.1016/J.JHAZMAT.2011.11.09710.1016/J.JHAZMAT.2011.11.097 ↗
46. A. Al-Nafiey, A. Kumar, M. Kumar, A. Addad, B. Sieber, S. Szunerits, R. Boukherroub, S.L. Jain, Nickel oxide nanoparticles grafted on reduced graphene oxide (RGO/NiO) as efficient photocatalyst for reduction of nitroaromatics under visible light irradiation. J. Photochem. Photobiol. Chem. 336, 198–207 (2017). https://doi.org/10.1016/j.jphotochem.2016.12.02310.1016/j.jphotochem.2016.12.023 ↗
47. F. Wang, D. Zhao, L. Zhang, L. Fan, X. Zhang, S. Hu, Nanostructured nickel nitride with reduced graphene oxide composite bifunctional electrocatalysts for an efficient. Nanomaterials (2019). https://doi.org/10.3390/nano911158310.3390/nano9111583 ↗
48. A. Roychoudhury, A. Prateek, S. Basu, S.K. Jha, Preparation and characterization of reduced graphene oxide supported nickel oxide nanoparticle-based platform for sensor applications. J. Nanopart. Res. 20(3), 1–17 (2018). https://doi.org/10.1007/S11051-018-4173-Y/METRICS10.1007/S11051-018-4173-Y/METRICS ↗
49. Y. Zhang, Y. Shen, X. Xie, W. Du, L. Kang, Y. Wang, B. Wang, One-step synthesis of the reduced graphene oxide@ NiO composites for supercapacitor electrodes by electrode-assisted plasma electrolysis. Mater. Design 196, 109111 (2020)10.1016/j.matdes.2020.109111 ↗
50. K. Bhowmik, A. Mukherjee, M.K. Mishra, G. De, Stable Ni nanoparticle-reduced graphene oxide composites for the reduction of highly toxic aqueous Cr(VI) at room temperature. Langmuir 30(11), 3209–3216 (2014). https://doi.org/10.1021/LA500156E/SUPPL_FILE/LA500156E_SI_001.PDF10.1021/LA500156E/SUPPL_FILE/LA500156E_SI_001.PDF ↗
51. K.B. Dhopte, R.S. Zambare, A.V. Patwardhan, P.R. Nemade, Role of graphene oxide as a heterogeneous acid catalyst and benign oxidant for synthesis of benzimidazoles and benzothiazoles. RSC Adv. 6(10), 8164–8172 (2016). https://doi.org/10.1039/C5RA19066E10.1039/C5RA19066E ↗
52. S. Kumar, N. Jangir, M.K. Samata, K. Kumar, D.K. Jangid, NiO heterogeneous nano-catalyst mediated simple, rapid and efficient synthesis of 2-aryl substituted benzothiazoles. RASĀYAN J. Chem. 17(4), 1579–1586 (2024). https://doi.org/10.31788/RJC.2024.174898210.31788/RJC.2024.1748982 ↗
53. S.M. Inamdar, V.K. More, S.K. Mandal, CuO nano-particles supported on silica, a new catalyst for facile synthesis of benzimidazoles, benzothiazoles and benzoxazoles. Tetrahedron Lett. 54(6), 579–583 (2013). https://doi.org/10.1016/J.TETLET.2012.11.09110.1016/J.TETLET.2012.11.091 ↗
54. H. Ghafuri, E. Esmaili, M. Talebi, 3O4@SiO2/collagen: An efficient magnetic nanocatalyst for the synthesis of benzimidazole and benzothiazole derivatives. Comptes Rendus Chim. 19(8), 942–950 (2016). https://doi.org/10.1016/j.crci.2016.05.00310.1016/j.crci.2016.05.003 ↗
55. A. Teimouri, A.N. Chermahini, H. Salavati, L. Ghorbanian, An efficient and one-pot synthesis of benzimidazoles, benzoxazoles, benzothiazoles and quinoxalines catalyzed via nano-solid acid catalysts. J. Mol. Catal. Chem. 373, 38–45 (2013). https://doi.org/10.1016/j.molcata.2013.02.03010.1016/j.molcata.2013.02.030 ↗
56. G.R. Bardajee, M. Mohammadi, H. Yari, A. Ghaedi, Simple and efficient protocol for the synthesis of benzoxazole, benzoimidazole and benzothiazole heterocycles using Fe(III)–Schiff base/SBA-15 as a nanocatalyst. Chin. Chem. Lett. 27(2), 265–270 (2016). https://doi.org/10.1016/j.cclet.2015.10.01110.1016/j.cclet.2015.10.011 ↗
57. Y. Cai, H. Yuan, Q. Gao et al., Palladium (II) complex supported on magnetic nanoparticles modified with phenanthroline: a highly active reusable nanocatalyst for the synthesis of benzoxazoles, benzothiazoles and cyanation of aryl halides. Catal. Lett. 153, 460–476 (2023). https://doi.org/10.1007/s10562-022-03990-910.1007/s10562-022-03990-9 ↗
58. M. Cellier, O.J. Fabrega, E. Fazackerley, A.L. James, S. Orenga, J.D. Perry, V.L. Salwatura, S.P. Stanforth, 2-arylbenzothiazole, benzoxazole and benzimidazole derivatives as fluorogenic substrates for the detection of nitroreductase and aminopeptidase activity in clinically important bacteria. Bioorgan. Med. Chem. (2011). https://doi.org/10.1016/j.bmc.2011.03.04310.1016/j.bmc.2011.03.043 ↗
59. K.B. Digambar, R. Varala, S.G. Patil, Zn(OAc)2. 2H2O: an efficient catalyst for the one-pot synthesis of 2-substituted benzothiazoles. Org. Commun. 15(4), 378–385 (2022). https://doi.org/10.25135/acg.oc.140.2210.261810.25135/acg.oc.140.2210.2618 ↗
60. Q.T. Nguyen, A.H. Thi Hang, T.L. Ho Nguyen, D.K. Nguyen Chau, P.H. Tran, Phosphonium acidic ionic liquid: an efficient and recyclable homogeneous catalyst for the synthesis of 2-arylbenzoxazoles, 2-arylbenzimidazoles, and 2-arylbenzothiazoles. RSC Adv. 8(21), 11834–11842 (2018). https://doi.org/10.1039/C8RA01709C10.1039/C8RA01709C ↗
61. A.K. Chakraborti, S. Rudrawar, K.B. Jadhav, G. Kaur, S.V. Chankeshwara, On water’ organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolines. Green. Chem. 9, 1335–1340 (2007). https://doi.org/10.1039/b710414f10.1039/b710414f ↗
62. K.N. Patil, R.K. Bhat, C.D. Bhenki, V.B. Helavi, Oxalic acid dihydrate: L-Proline (LTTM) mediated synthesis of 2-substituted benzothiazole derivatives. Chem. Data Collect. 24, 100307 (2019). https://doi.org/10.1016/J.CDC.2019.10030710.1016/J.CDC.2019.100307 ↗
63. R. Sirgamalla, A. Kommakula, S. Konduru, R. Ponakanti, J. Devaram, S. Boda, Cupper-catalyzed an efficient synthesis, characterization of 2-substituted benzoxazoles, 2-substituted benzothiazoles derivatives and their anti-fungal activity. Chem. Data Collect. 27, 100362 (2020). https://doi.org/10.1016/j.cdc.2020.10036210.1016/j.cdc.2020.100362 ↗