One-pot synthesis of fully substituted 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, cyclobutanone and N-isocyaniminotriphenylphosphorane

Reactions of N-isocyaniminotriphenylphosphorane with cyclobutanone in the presence of aromatic (or heteroaromatic) carboxylic acids proceeded smoothly at room temperature and in neutral conditions to afford sterically congested 1-(5-aryl-1,3,4-oxadiazol-2-yl)- 1-cyclobutanol derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed. The structures of the products were deduced from their IR, 1HNMR, and 13CNMR spectra, and mass spectrometry.

One-pot synthesis of fully substituted 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, cyclobutanone and N -isocyaniminotriphenylphosphorane

Reactions of N-isocyaniminotriphenylphosphorane with cyclobutanone in the presence of aromatic (or heteroaromatic) carboxylic acids proceeded smoothly at room temperature and in neutral conditions to afford sterically congested 1-(5-aryl-1,3,4-oxadiazol-2-yl)- 1-cyclobutanol derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed. The structures of the products were deduced from their IR, 1HNMR, and 13CNMR spectra, and mass spectrometry.

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  • new synthetic approach discussed here has potential in synthesis of various 2,5-disubstituted 1,3,4-oxadiazoles, which are of considerable interest as potential biologically active compounds or pharmaceuticals. Ramazani, A.; Nasrabadi, F. Z.; Karimi, Z.; Rouhani, M. Bull. Korean Chem. Soc. 2011, 32, 2700-2704. a) Ramazani, A.; Kazemizadeh, A. R.; Ahmadi, E.; Noshiranzadeh N.; Souldozi, A.
  • Curr. Org. Chem. 2008 12 59-82; b) Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, , 2663-2666; c) Ramazani, A.; Ahmadi, E. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 178, 2659-2661; d)
  • Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2004, 179, 529-534; e) Ramazani, A.; Bodaghi,
  • A. Phosphorus, Sulfur, Silicon Relat. Elem. 2004, 179, 1615-1620; f) Ramazani, A.; Kazemizadeh, A. R.; Ahmadi,
  • E. Phosphorus, Sulfur, Silicon Relat. Elem. 2005, 180, 1781-1784; g) Ramazani, A.; Azizian, A.; Bandpey, M.;
  • Noshiranzadeh, N. Phosphorus, Sulfur, Silicon Relat. Elem. 2006, 181, 2731-2734; h) Ramazani, A.; Ahmadi, E.
  • Phosphorus, Sulfur, Silicon Relat. Elem. 2006, 181, 2725-2729. 3. a) Ramazani, A.; Kazemizadeh, A. R.; Ahmadi, E.; Slepokura, K.; Lis, T. Z. Naturforsch. 2006 61b, 1128-1133; b) Ramazani, A.; Noshiranzadeh, N.; Ghamkhari, A.; ´S lepokura, K.; Lis, T. Helv. Chim. Acta 2008, 91, 2252-2261
  • Ramazani, A.; Farshadi, A.; Mahyari, A.; lepokura, K.; Lis, T.; Rouhani, M.; J. Chem. Crystallogr. 2011, 41, 1385.
  • Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197-1218
  • Palacios, F.; Aparicio, D.; Rubiales, G.; Alonso, C.; de los Santos, J. M. Curr. Org. Chem. 2009 13, 810-828
  • Palacios, F.; Aparicio, D.; Rubiales, G.; Alonso, C.; de los Santos, J. M. Curr. Org. Chem. 2006, 10, 2371-2392
  • Haj´os, G.; Nagy, I. Curr. Org. Chem. 2008, 12, 39-58
  • Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de los Santos, J. M. Tetrahedron 2007, 63, 523-575
  • Cossio, F. P.; Alonso, C.; Lecea, B.; Ayerbe, M.; Rubiales, G.; Palacios, F. J. Org. Chem. 2006, 71, 2839-2847
  • Palacios, F.; Herr´an, E.; Alonso, C.; Rubiales, G.; Lecea, B.; Ayerbe, M.; Coss´ıo, F. P. J. Org. Chem. 2006, 71, 6020-6030
  • Stolzenberg, H.; Weinberger, B.; Fehlhammer, W. P.; P¨uhlhofer, F. G.; Weiss, R. Eur. J. Inorg. Chem. 2005, 21, 4271.
  • Chiu, T. W.; Liu, Y. H.; Chi, K. M.; Wen, Y. S.; Lu, K. L. Inorg Chem 2005, 44, 6425-6430.
  • Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 178, 1325-1328.
  • Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 178, 1329-1332.
  • Ramazani, A.; Bodaghi, A. Tetrahedron Lett. 2000, 41, 567-568
  • Pakravan, P.; Ramazani, A.; Noshiranzadeh, N.; Sedrpoushan, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, , 545-549
  • Ramazani, A.; Rahimifard, M.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, 182, 1-5.
  • Ramazani, A.; Rahimifard, M.; Noshiranzadeh, N.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, 413-417
  • Ramazani, A.; Ahmadi, E.; Kazemizadeh, A. R.; Dolatyari, L.; Noshiranzadeh, N.; Eskandari, I.; Souldozi, A. Phosphorus, Sulphur, Silicon Relat. Elem 2005, 180, 2419-2422
  • Ramazani, A.; Mohammadi-Vala, M. A. Phosphorus, Sulfur, Silicon Relat. Elem. 2001, 176, 223-229
  • Ramazani, A.; Amini, I.; Massoudi, A. Phosphorus, Sulphur, Silicon Relat. Elem. 2006, 181, 2225-2229 a) Souldozi, A.; Ramazani, A.; Bouslimani, N.; Welter, R. Tetrahedron Lett. 2007, 48, 2617-2620; b) Ramazani, A.;
  • Rouhani, M.; Rezaei, A.; Shajari, N.; Souldozi, A. Helv. Chim. Acta 2011, 94, 282-288; c) Ramazani, A.; Shajari,
  • N.; Mahyari, A.; Ahmadi, Y. Mol. Divers. 2011, 15, 521-527; d) Nasrabadi, F. Z.; Ramazani, A.; Ahmadi, Y. Mol. Divers. 2011 15 791-798. a) Souldozi, A.; Ramazani, A. Tetrahedron Lett. 2007, 48, 1549-1551; b) Ramazani, A.; Nasrabadi, F. Z.; Mashhadi
  • Malekzadeh, A.; Ahmadi, Y. Monatsh. Chem. 2011, 142, 625630 a) Souldozi, A.; Ramazani, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2009 184, 3191-3198; b) Ramazani, A.;
  • Ahmadi, Y.; Rouhani, M.; Shajari, N.; Souldozi, A. Heteroatom Chem. 2010, 21, 368-372 a) Souldozi, A.; Ramazani, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2009 184, 2344-2350; b) Ramazani, A.;
  • Ahmadi, Y.; Tarasi, R. Heteroatom Chem. 2011, 22 79-84
  • Souldozi, A.; Ramazani, A. Arkivoc 2008, xvi, 235-242
  • Ramazani, A.; Salmanpour, S.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2010, 185, 97-102
  • Souldozi, A.; lepokura, K.; Lis, T.; Ramazani, A. Z. Naturforsch. 2007, 62b, 835-840.
  • Ramazani, A.; Morsali, A.; Ganjeie, B.; Kazemizadeh, A. R.; Ahmadi, E.; Kempe, R.; Hertle, I. Z. Naturforsch. , 60b, 569-571. Ramazani, A.; Rezaei, A. Org. Lett. 2010, 12 2852-2855.
  • Holla, B. S.; Gonsalves, R.; Shenoy, S. Eur. J. Med. Chem. 2000, 35, 267-271.
  • Chen, Q.; Zhu, X. –H.; Jiang, L. –L.; Liu, Z. –M.; Yang, G. –F. Eur. J. Med. Chem. 2008, 43, 595-603
  • Amir, M.; Shikha, K. Eur. J. Med. Chem. 2004, 39, 535-545
  • Baxendale, I. R. ; Ley, S. V. ; Martinelli, M. Tetrahedron 2005, 61, 5323-5349
  • Coppo, F. T.; Evans, K. A.; Graybill, T. L.; Burton, G. Tetrahedron Lett. 2004, 45, 3257-3260
  • Brain, C. T.; Paul, J. M.; Loong, Y.; Oakley, P. J. Tetrahedron Lett. 1999, 40, 3275-3278
  • Wang, Y.; Sauer, D. R.; Djuric, S. W. Tetrahedron Lett. 2006, 47, 105-108
Turkish Journal of Chemistry-Cover
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