10.1007/s40097-014-0129-7

Facile microwave-assisted synthesis of 2-aryloxazolo[4,5-b]pyridines using SBA-Pr-NH2

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  • Ghodsi Mohammadi Ziarani*1,
  • Monireh Shakiba Nahad1,
  • Negar Lashgari2,
  • Alireza Badiei2,
  1. Department of Chemistry, Alzahra University, Tehran, IR
  2. School of Chemistry, College of Science, University of Tehran, Tehran, IR
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Published in Issue 07-10-2014

How to Cite

Mohammadi Ziarani, G., Shakiba Nahad, M., Lashgari, N., & Badiei, A. (2014). Facile microwave-assisted synthesis of 2-aryloxazolo[4,5-b]pyridines using SBA-Pr-NH2. Journal of Nanostructure in Chemistry, 5(1 (March 2015). https://doi.org/10.1007/s40097-014-0129-7
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Abstract

Abstract Abstract In this work, amino-functionalized SBA-15 (SBA-Pr-NH 2 ) has been used as a basic nano-catalyst in the one-pot synthesis of 2-aryloxazolo[4,5- b ]pyridines by the condensation reaction of 2-amino-3-hydroxypyridine and benzoyl chlorides under microwave irradiation in solvent free conditions. Among the advantages of this work are short reaction times, high yields and simple work-up. SBA-Pr-NH 2 as an efficient heterogeneous nanoporous solid basic catalyst which was prepared by silica functionalization with 3-aminopropyltriethoxysilane, can be easily removed from the reaction mixture by simple filtration, and also recovered and reused without noticeable loss of reactivity. 2-Aryloxazolo[4,5- b ]pyridines have different pharmacological activities (anti-inflammatory, anti-pyretic, analgesic, antifungal). In the current method for the synthesis of 2-aryloxazolo[4,5- b ]pyridines, no hazardous organic solvent was used and simplicity of the procedure provides significant improvements over many of other existing methods. Furthermore, the SBA-15-Pr-NH 2 with pore size of 6 nm can act as nano-reactor. Graphical Abstract

Keywords

  • 2-Aryloxazolo[4,5-b]pyridines,
  • SBA-Pr-NH2,
  • Microwave irradiation,
  • 2-Amino-3-hydroxypyridine,
  • Nano-reactor
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References

  1. Mac et al. (2007) Fluorescence properties of the derivatives of oxazolo[4,5-b]pyridyne (pp. 188-196) https://doi.org/10.1016/j.jphotochem.2007.05.023
  2. Marie-Claude et al. (1997) Acylation of oxazolo[4,5-b]pyridin-2(3H)-ones, 2-phenyloxazolo[4,5-b]pyridines and pyrrolo[2,3-b]pyridin-2(2H)-ones (pp. 5159-5168) https://doi.org/10.1016/S0040-4020(97)00179-8
  3. Viaud et al. (1995) N-substituted aminohydroxypyridines as potential non-opioid analgesic agents (pp. 929-937) https://doi.org/10.1016/0968-0896(95)00080-Z
  4. Duchowicz et al. (2007) QSAR analysis for heterocyclic antifungals (pp. 2680-2689) https://doi.org/10.1016/j.bmc.2007.01.039
  5. Zhuravlev (2006) Unprecedentedly mild direct Pd-catalyzed arylation of oxazolo[4,5-b]pyridine (pp. 2929-2932) https://doi.org/10.1016/j.tetlet.2006.02.117
  6. Maryanoff and Costanzo (2008) Inhibitors of proteases and amide hydrolases that employ an α-ketoheterocycle as a key enabling functionality (pp. 1562-1595) https://doi.org/10.1016/j.bmc.2007.11.015
  7. Mincheva et al. (2005) Fosmidomycin analogues as inhibitors of monoterpenoid indole alkaloid production in Catharanthus roseus cells (pp. 1797-1803) https://doi.org/10.1016/j.phytochem.2005.06.002
  8. Marco et al. (2004) Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors (pp. 2199-2218) https://doi.org/10.1016/j.bmc.2004.02.017
  9. Bemis et al. (2009) Discovery of oxazolo[4,5-b]pyridines and related heterocyclic analogs as novel SIRT1 activators (pp. 2350-2353) https://doi.org/10.1016/j.bmcl.2008.11.106
  10. Barni et al. (1985) Disperse and cationic dyes from 2-(o, m, p-Aminophenyl)oxazolo [4,5-b]pyridine (pp. 1-12) https://doi.org/10.1016/0143-7208(85)80001-2
  11. Heuser et al. (2005) New facile and mild synthesis of 2-substituted oxazolopyridines (pp. 9001-9004) https://doi.org/10.1016/j.tetlet.2005.10.109
  12. Ge et al. (2007) One-pot synthesis of 2-trifluoromethyl and 2-difluoromethyl substituted benzo-1,3-diazoles (pp. 3251-3254) https://doi.org/10.1016/j.tetlet.2007.03.015
  13. Myllymäki and Koskinen (2007) A rapid method for the preparation of 2-substituted oxazolo[4,5-b]pyridines using microwave-assisted direct condensation reactions (pp. 2295-2298) https://doi.org/10.1016/j.tetlet.2007.01.161
  14. Mohammadpoor-Baltork et al. (2007) ZrOCl2·8H2O as an efficient, environmentally friendly and reusable catalyst for synthesis of benzoxazoles, benzothiazoles, benzimidazoles and oxazolo[4,5-b]pyridines under solvent-free conditions (pp. 1865-1870) https://doi.org/10.1016/j.catcom.2007.02.020
  15. Mohammadi Ziarani et al. (2014) A simple and clean method for multicomponent synthesis of spiro[indole-tetrahydropyrano(2,3-d)pyrimidine] derivatives using SBA-Pr-SO3H as catalyst under solvent-free conditions (pp. 701-709) https://doi.org/10.1007/s13738-013-0342-1
  16. Song et al. (2005) Functionalized SBA-15 materials as carriers for controlled drug delivery: influence of surface properties on matrix–drug interactions (pp. 9568-9575) https://doi.org/10.1021/la051167e
  17. Jung et al. (2011) Synthesis of TiO2 supported on SBA-15 using different method and their photocatalytic activity (pp. 7446-7450) https://doi.org/10.1166/jnn.2011.4765
  18. Bruhwiler (2010) Postsynthetic functionalization of mesoporous silica (pp. 887-892) https://doi.org/10.1039/c0nr00039f
  19. Mohammadi Ziarani et al. (2012) Application of amino-functionalized SBA-15 type mesoporous silica in one-pot synthesis of spirooxindoles (pp. 1832-1839) https://doi.org/10.1016/S1872-2067(11)60456-7
  20. Chen et al. (2012) Synthesis and catalytic activity of amino-functionalized SBA-15 materials with controllable channel lengths and amino loadings (pp. 2233-2243) https://doi.org/10.1039/C2JM14393C
  21. Mohammadi Ziarani et al. (2013) Efficient one-pot synthesis of bis(4-hydroxycoumarin)methanes in the presence of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) (pp. 499-502) https://doi.org/10.1002/jccs.201200530
  22. Mohammadi Ziarani et al. (2013) Green synthesis of spiro[indoline-3,9′-xanthene]trione derivatives using sulfonic acid functionalized SBA-15 as a new nanoporous acid catalyst (pp. 580-586)
  23. Mohammadi Ziarani et al. (2010) One pot synthesis of polyhydroquinolines catalyzed by sulfonic acid functionalized SBA-15 as a new nanoporous acid catalyst under solvent free conditions (pp. 1-10)
  24. Clark et al. (1978) 2-(Substituted phenyl)oxazolo[4,5-b]pyridines and 2-(substituted phenyl)oxazolo[5,4-b]pyridines as nonacidic antiinflammatory agents (pp. 1158-1162) https://doi.org/10.1021/jm00209a014
  25. Guillaumet, G., Flouzat, C.: Process for the synthesis of oxazolopyridine compounds. US Patent, US 5077408 A (1991)
  26. Shen, T.Y., Clark, R.L., Pessolano, A.A., Witzel, B.E., Lanza, T.J.: Anti-inflammatory oxazole[4,5-b]pyridines. US Patent, US4038396 A (1977)
  27. Doise et al. (1990) Synthesis of novel heterocycles: oxazolo[4,5-b]pyridines and oxazolo[4,5-d]pyrimidines (pp. 1155-1156) https://doi.org/10.1016/S0040-4039(00)88750-X
  28. Badiei et al. (2011) A novel method for preparation of 8-hydroxyquinoline functionalized mesoporous silica: aluminum complexes and photoluminescence studies (pp. 4912-4918) https://doi.org/10.1016/j.apsusc.2010.12.146