Salicylic acid as an efficient catalyst for the diastereoselective synthesis of dispirohydroquinolines via a one-pot domino eight-component reaction

  1. Sajjad Salahi
  2. Nourallah Hazeri
  3. Malek Taher Maghsoodlou
  4. Mojtaba Lashkari
  5. Niloufar Akbarzadeh Torbati
  6. Santiago García-Granda
  7. Laura Torre-Fernández
Revista:
Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química)

Año de publicación: 2018

Volumen: 63

Número: 4

Páginas: 4159-4164

Tipo: Artículo

DOI: 10.4067/S0717-97072018000404159 DIALNET GOOGLE SCHOLAR lock_openAcceso abierto editor

Resumen

Salicylic acid was used as an efficient catalyst for the diastereoselective synthesis of dispirohydroquinoline-bis (Meldrim's acid) derivatives via a one-pot domino eight-component reaction of arylamines, aromatic aldehydes and Meldrum's acid in CH3CN at room temperature. The remarkable advantages offered by this method are inexpensive catalyst, good yields, simple and easy work-up procedure. The characterization of products was done by IR, mass, 1H NMR, 13C NMR spectroscopy, and elemental analyses. The stereoselectivity of compounds was confirmed with crystallography and NMR spectroscopy.

Referencias bibliográficas

  • Dömling, A.. (2006). Chem. Rev. 106. 17
  • Orru, R.V.A.,de Greef, M.. (2003). Synthesis. 10. 1471
  • Hulme, C.,Gore, V.. (2003). Curr. Med. Chem. 10. 51
  • Montagne, C.,Shiers, J.J,Shipman, M.. (2006). Tetrahedron Lett. 47. 9207
  • Carling, R.W.,Leeson, P.D.,Moseley, A.M.,Baker, R.,Forster, A.C.,Grimwood, S.,Kemp, J.A.,Marshall, G.R.. (1992). J. Med. Chem. 35. 1942
  • Cai, S. X.,Zhou, Z-L.,Huang, J-C.,Whittermore, E.R.,Egbuwoku, Z.O.,Hawkinson, J.E.,Woodward, R.M.,Keana, J.F.. (1996). J. Med. Chem. 39. 3248
  • Jacquemond-Collet, I.,Benoit-Vical, F.,Valentin, A.,Stanislas, E.,Mallie, M.,Fouraste, I.. (2002). Planta Med. 68. 68
  • Wallace, O.B.,Lauwers, K.S.,Jones, S.A.,Dodge, J.A.. (2003). Bioorg. Med. Chem. Lett. 13. 1907
  • Jacobs, C.,Frotscher, M.,Dannhardt, G.,Hartmann, R.W.. (2000). J. Med. Chem. 43. 1841
  • Dorey, G.,Lockhart, B.,Lestage, P.,Casara, P.. (2000). Bioorg. Med. Chem. Lett. 10. 935
  • Nishiyama, T.T.,Hashiguchi, Y.Y.,Sakata, S.T.,Sakaguchi, T.T.. (2003). Polym. Degrad. Stab. 79. 225
  • Calhoun, W.,Carlson, R.P.,Crossley, R.,Datko, L.J.,Dietrich, S.,Heatherington, K.,Marshall, L.A.,Meade, P.J.,Opalko, A.,Shepherd, R.G.. (1995). J. Med. Chem. 38. 1473
  • Schmittel, M.,Strittmatter, M.,Vollmann, K.,Kiau, S.. (1996). Tetrahedron Lett. 37. 999
  • Etman, H.A.,Sofan, M.A.,Metwally, M.A.. (1995). Boll. Chim. Farm. 134. 249
  • Hazeri, N.,Maghsoodlou, M. T.,Habibi-Khorassani, S. M.,Marandi, G.,Khandan-Barani, K.,Ziyaadini, M.,Aminkhani, A.. (2007). ARKIVOC. 173
  • Maghsoodlou, M.T.,Habibi-Khorassani, S.M.,Moradi, A.,Hazeri, N.,Davodi, A.,Sajadikhah, S. S.. (2011). Tetrahedron. 67. 8492
  • Maghsoodlou, M.T.,Habibi-Khorassani, S.M.,Heydari, R.,Rostami-Charati, F.,Hazeri, N.,Lashkari, M.,Rostamizadeh, M.,Marandi, G.,Sobolev, A.,Makha, M.. (2009). Tetrahedron Lett. 50. 4439
  • Hazeri, N.,Maghsoodlou, M.T.,Habibi-Khorassani, S.M.,Ziyaadini, M.,Marandi, G.,Khandan-Barani, K.,Bijanzadeh, H.R.. (2007). ARKIVOC. 34
  • Salahi, S.,Maghsoodlou, M. T.,Hazeri, N.,Lashkari, M.,Akbarzadeh Torbati, N.,Kazemian, M.A.,García-Granda, S.,Torre-Fernández, L.. (2016). J. Saudi Chem. Soc. 20. 349
  • Salahi, S.,Maghsoodlou, M. T.,Hazeri, N.,Lashkari, M.,Garcia-Granda, S.,Torre-Fernandez, L.. (2015). Chin. J. Catal. 36. 1023
  • Lashkari, M.,Maghsoodlou, M.T.,Hazeri, N.,Habibi-Khorassani, S.M.,Akbarzadeh-Torbati, N.,García-Granda, S.,Torre-Fernández, L.. (2015). J. Heterocyclic Chem. 52. 873
  • Salahi, S.,Hazeri, N.,Maghsoodlou, M.T.,García-Granda, S.,Torre-Fernández, L.. (2014). J. Chem. Res. 38. 383
  • Hazeri, N.,Lashkari, M.,García-Granda, S.,Torre-Fernández, L.. (2014). Aust. J. Chem. 67. 1656
  • Ramachary, D.B.,Chowdari, N.S.,Barbas III, C.F.. (2003). Angew. Chem. Int. Ed. 42. 4233
  • Ramachary, D.B.,Anebousely, K.,Chowdari, N.S.,Barbas III, C.F.. (2004). J. Org. Chem. 69. 5838
  • Ramachary, D.B.,Chowdari, N.S.,Barbas III, C.F.. (2003). Synlett. 12. 1910
  • Jiang, B.,Hao, W.-J.,Zhang, J.-P.,Tu, S.-J.,Shi, F.. (2009). Org. Biomol. Chem. 7. 2195
  • Shults, E.S.,Semenov, E.A.,Johnson, A.A.,Bondarenko, S.P.,Bagryanskaya, I.Y.,Gatilov, Y.V.,Tolstikov, G.A.,Pommier, Y.. (2007). Bioorg. Med. Chem. Lett. 17. 1362
  • Shi, J.,Liu, Y.,Wang, M.,Lin, L.,Liu, X.,Feng, X.. (2011). Tetrahedron. 67. 1781
  • Pizzirani, D.,Roberti, M.,Recanatini, M.. (2007). Tetrahedron Lett. 48. 7120
  • Hao, W.-J.,Bo Jiang, B.,Tu, S.-J.,Wu, S.-S.,Han, Z.-G.,Cao, X.-D.,Zhang, X.-H.,Yan, S.,Shi, F.. (2009). J. Comb. Chem. 11. 310
  • Pizzirani, D.,Roberti, M.,Grimaudo, S.,Di Cristina, A.,Pipitone, R.M.,Tolomeo, M.,Recanatini, M.. (2009). J. Med. Chem. 52. 6936
  • Wang, P.,Song, L.,Yi, H.,Zhang, M.,Zhu, S.,Deng, H.,Shao, M.. (2010). Tetrahedron Lett. 51. 3975
  • Tu, S.-J.,Zhu, X.,Zhang, J.,Xu, J.,Zhang, Y.,Wang, Q.,Jia, R.,Jiang, B.,Zhang, J.,Yao, C.. (2006). Bioorg. Med. Chem. Lett. 16. 2925
  • Wang, X.-S.,Zhang, M.-M.,Jiang, H.,Yao, C.-S.,Tu, S.-J.. (2007). Tetrahedron. 21. 4439
  • Sun, J.,Xia, E.-Y.,Wu, Q.,Yan, C.-G.. (2011). ACS Comb. Sci. 13. 421
  • (2013). Agilent CrysAlis PRO. Agilent Technologies UK Ltd. Yarnton, England.
  • Burla, M.C.,Caliandro, R.,Camalli, M.,Carrozzini, B.,Cascarano, G.L.,Giacovazzo, C.,Mallamo, M.,Mazzone, A.,Polidori, G.,Spagna, R.. (2012). J. Appl. Cryst. 45. 357
  • Sheldrick, G.M.. (2008). Acta Cryst. 64. 112
  • Farrugia, L.J.. (1997). J. Appl. Cryst. 30. 565
  • Farrugia, L.J.. (1999). J. Appl. Cryst. 32. 837
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