Issue

Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018

Copyright (c) 2018 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

A Rapid Phase Transfer Catalyzed Heteroarylation by C-O Coupling and Ring Opening of Isopropylidene Glycerol in Synthesis of (Pyrazolopyrimidin-4-yloxy)propane-1,2-diols

https://doi.org/10.14233/ajchem.2018.21576
Vivek C. Ramani
Department of Chemistry, M.G. Science Institute, Ahmedabad-380 006, India
Nirmal M. Shah
Department of Chemistry, M.G. Science Institute, Ahmedabad-380 006, India
Rina D. Shah
Department of Chemistry, M.G. Science Institute, Ahmedabad-380 006, India

Corresponding Author(s) : Rina D. Shah

drrdshah@yahoo.co.in

Asian Journal of Chemistry, Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018

Abstract

A comparative study of C-O cross coupling reaction in synthesis of 4-(O,O-isopropylidene-2,3-dihydroxypropoxypyrazolo[3,4-d]-pyrimidines (3) has been under taken using phase transfer catalysis. Liquid-liquid phase transfer catalysis has been explored in reaction between (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (1) and 4-chloropyrazolo[3,4-d]pyrimidines (2) using tetrabutylammonium bromide (TBAB) as phase transfer catalyst, aqueous NaOH as inorganic phase and chlorobenzene as organic phase at room temperature to form 3. Ring opening of (2,2-dimethyl-1,3-dioxolan-4-yl)methanolyl present in 3 under acidic hydrolysis at room temperature afforded 3-(1,6-disubstituted 1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propane-1,2-diols (4).

Keywords

C-O cross coupling O-arylation Liquid-liquid phase transfer catalysis Isopropylidene glycerol
Ramani, V. C., Shah, N. M., & Shah, R. D. (2018). A Rapid Phase Transfer Catalyzed Heteroarylation by C-O Coupling and Ring Opening of Isopropylidene Glycerol in Synthesis of (Pyrazolopyrimidin-4-yloxy)propane-1,2-diols. Asian Journal of Chemistry, 30(10), 2352–2356. https://doi.org/10.14233/ajchem.2018.21576
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. M. Makosza and M. Ludwikow, Angew. Chem. Int. Ed. Eng., 13, 665 (1974); https://doi.org/10.1002/anie.197406651.
  2. M. Ikunaka, Org. Progr. Res. Dev., 12, 698 (2008); https://doi.org/10.1021/op700262h.
  3. S. D’Antone, M. Penco, R. Solaro and E. Chiellini, React. Polym. Ion Exchang. Sorbents, 3, 107 (1985); https://doi.org/10.1016/0167-6989(85)90054-6.
  4. J. A. Zoltewicz, eds.: R.D. Rieke, J.A. Zoltewicz, H.G. Aurich, W. Weiss and K.P.C. Vollhardt, New Directions in Aromatic Nucleophilic Substitution, In: Organic Synthesis, John Wiley & Sons Inc., SpringerVerlag: Berlin/Heidelberg, pp. 33–64 (1975).
  5. K. Urata and N. Takaishi, J. Am. Oil Chem. Soc., 71, 1027 (1994); https://doi.org/10.1007/BF02542274.
  6. M. Sutter, E. D. Silva, N. Duguet, Y. Raoul, E. Métay and M. Lemaire, Chem. Rev., 115, 8609 (2015) https://doi.org/10.1021/cr5004002.
  7. M. Renoll and M.S. Newman, DL-Isopropylideneglycerol: Glycerol, isopropylidene-; also 1,3-dioxolane-4-methanol, 2,2-dimethyl-, In: Organic Synthesis, John Wiley & Sons Inc., pp. 73–73 (2003). https://doi.org/10.1002/0471264180.os028.29.
  8. E. De Clercq and A. Holy, J. Med. Chem., 22, 510 (1979); https://doi.org/10.1021/jm00191a010.
  9. A. Behr, J. Eilting, K. Irawadi, J. Leschinski and F. Lindner, Green Chem., 10, 13 (2008); https://doi.org/10.1039/B710561D.
  10. J.-F. Griffon, A. Dumas, R. Storer, J.-P. Sommadossi and G. Gosselin, Nuclos. Nucleot. Nucl. Acids, 28, 435 (2009); https://doi.org/10.1080/15257770903044531.
  11. S. Bailey, M.R. Harnden, R.L. Jarvest, A. Parkin and M.R. Boyd, J. Med. Chem., 34, 57 (1991); https://doi.org/10.1021/jm00105a010.
  12. C.G. Dave and R.D. Shah, J. Heterocycl. Chem., 35, 1295 (1998); https://doi.org/10.1002/jhet.5570350609.
  13. C.G. Dave and R.D. Shah, Molecules, 7, 554 (2002); https://doi.org/10.3390/70700554.
  14. R.D. Shah, Chem. Sustain. Dev., 19, 319 (2011).
  15. N. Desai and R. Shah, Synthesis, 3275 (2006); https://doi.org/10.1055/s-2006-950206.
  16. R.D. Shah and N.M. Shah, Int. Res. J. Nat. Appl. Sci., 4, 21 (2017).
  17. A. Mattarei, A. Rossa, V. Bombardelli, M. Azzolini, M. La Spina, C. Paradisi, M. Zoratti and L. Biasutto, Eur.J. Med. Chem., 135, 77 (2017); https://doi.org/10.1016/j.ejmech.2017.04.034.
  18. J. Hert, D. Hunziker, H. Kuehne, T. Luebbers, R.E. Martin, P. Mattei, W. Neidhart, H. Richter, M. Rudolph and E. Pinard, Phenoxymethyl Derivatives, WO/2017/037146 (2017).
  19. M. Pagliaro, R. Ciriminna, H. Kimura, M. Rossi and C. Della-Pina, Angew. Chem. Int. Ed., 46, 4434 (2007); https://doi.org/10.1002/anie.200604694.
  20. L.M. Toledo, N.B. Lydon and D. Elbaum, Curr. Med. Chem., 6, 775 (1999); https://doi.org/10.1002/chin.199946289.
  21. L. Moity, A. Benazzouz, V. Molinier, V. Nardello-Rataj, M.K. Elmkaddem, P. de Caro, S. Thiébaud-Roux, V. Gerbaud, P. Marion and J.-M. Aubry, Green Chem., 17, 1779 (2015); https://doi.org/10.1039/C4GC02377C.
  22. J.A. Kenar, Lipid Technol., 19, 249 (2007); https://doi.org/10.1002/lite.200700079.
  23. V. Breu, M. Clozel, K. Burri, G. Hirth, W. Neidhart and H. Ramuz, FEBS Lett., 383, 37 (1996); https://doi.org/10.1016/0014-5793(96)00213-X.
  24. A.A.-H. Abdel-Rahman, A.-A.S. El-Etrawy, A.E.-S. Abdel-Megied, I.F. Zeid and E.S.H. El Ashry, Nuclos. Nucleot. Nucl. Acids, 27, 1257 (2008); https://doi.org/10.1080/15257770802086898.
  25. E.S.H. El Ashry, A.A.-H. Abdel-Rahman, N. Rashed and H.A. Rasheed, Arch. Pharm., 332, 327 (1999); https://doi.org/10.1002/(SICI)1521-4184(19999)332:9<327::AIDARDP327>3.0.CO;2-N.
  26. Y. Ouyang, H. Yang, P. Zhang, Y. Wang, S. Kaur, X. Zhu, Z. Wang, Y. Sun, W. Hong, Y. Ngeow and H. Wang, Molecules, 22, 1592 (2017); https://doi.org/10.3390/molecules22101592.
  27. D. Bakhotmah, R. Abdul-Rahman and M. Fakhorji, World J. Org. Chem., 5, 1 (2017).
  28. S. Mohana Roopan and R. Sompalle, Synth. Commun., 46, 645 (2016); https://doi.org/10.1080/00397911.2016.1165254.
  29. A.E. Rashad, M. Abdelmegid, A.H. Shamroukh and F.M.E. Abdelmegeid, Org. Chemistry: An Indian J., 10, 224 (2014).
  30. A.H. Abdelazeem, S.A. Abdelatef, M.T. El-Saadi, H.A. Omar, S.I. Khan, C.R. McCurdy and S.M. El-Moghazy, Eur. J. Pharm. Sci., 62, 197 (2014); https://doi.org/10.1016/j.ejps.2014.05.025.
  31. F. Gatta, F. Perotti, L. Gradoni, M. Gramiccia, S. Orsini, G. Palazzo and V. Rossi, Eur. J. Med. Chem., 25, 419 (1990); https://doi.org/10.1016/0223-5234(90)90005-N.
  32. C.C. Cheng and R.K. Robins, J. Org. Chem., 21, 1240 (1956); https://doi.org/10.1021/jo01117a010.
  33. J.J. Baldwin, W.C. Lumma, G.F. Lundell, G.S. Ponticello, A.W. Raab, E.L. Engelhardt, R. Hirschmann, C.S. Sweet and A. Scriabine, J. Med. Chem., 22, 1284 (1979); https://doi.org/10.1021/jm00197a002.
  34. C. Morrill, S. Babu, N. Almstead and Y.-C. Moon, Synthesis, 1791 (2013); https://doi.org/10.1055/s-0033-1338862.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0