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Production of pyrans, pyridazines, pyrimidines, pyrazines and triazine compounds using benzoylacetonitriles as a precursor

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Abstract

Benzoylacetonitriles are easily available and have high chemical reactivity due to the presence of three active moieties; nitrile, carbonyl, and active methylene functions. This review article represents a survey covering the synthetic strategies leading to five six-membered heterocycles; pyrans, pyridazines, pyrimidines, pyrazines, and triazine compounds; utilizing benzoylacetonitriles as starting precursor since 1985. The reactions are subdivided into groups that cover the synthetic methods of these heterocycles.

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References

  1. F. Al-Omran, A.A. El-Khair, J. Heterocycl. Chem. 41, 909 (2004)

    Article  CAS  Google Scholar 

  2. F. Al-Omran, A.A. El-Khair, J. Heterocycl. Chem. 41, 327 (2004)

    Article  CAS  Google Scholar 

  3. F. Al-Omran, A.A. El-Khair, J. Heterocycl. Chem. 44, 561 (2007)

    Article  CAS  Google Scholar 

  4. R. Ranjbar-Karimi, S. Hashemi-Uderji, M. Mousavi, J. Iran. Chem. Soc. 8, 193 (2011)

    Article  CAS  Google Scholar 

  5. M. Hosseini-Sarvari, J. Iran. Chem. Soc. 9, 535 (2012)

    Article  CAS  Google Scholar 

  6. P. Barraja, P. Diana, A. Lauria, A. Montalbano, A.M. Almerico, G. Dattolo, G. Cirrincione, G. Viola, F. Dall’Acqua, Bioorg. Med. Chem. Lett. 13, 2809 (2003)

    Article  CAS  Google Scholar 

  7. B. Zarranz, A. Jaso, I. Aldana, A. Monge, S. Maurel, E. Deharo, V. Jullian, M. Sauvain, Arzneimittel Forsch 55,754 (2005); B. Zarranz, A. Jaso, I. Aldana, A. Monge, S. Maurel, E. Deharo, V. Jullian, M. Sauvain, Chem. Abstr. 144, 266586 (2006)

    Google Scholar 

  8. R.E. Khidre, B.F. Abdel-Wahab, F.A.-R. Badria, Lett. Drug Design Discov. 8, 640 (2011)

    Article  CAS  Google Scholar 

  9. F. Al-Omran, A.-Z.A. Elassar, A.A. El-Khair, Tetrahedron 57, 10163 (2001)

    Article  CAS  Google Scholar 

  10. N.R. Mohamed, N.Y. Khaireldin, A.F. Fahmy, A.A. El-Sayed, Pharm. Chem. 2, 400 (2010)

    CAS  Google Scholar 

  11. E. Vicente, P.R. Duchowicz, D. Benitez, E.A. Castro, H. Cerecetto, M. Gonzalez, A. Monge, Bioorg. Med. Chem. Lett. 20, 4831 (2010)

    Article  CAS  Google Scholar 

  12. T.A. Farghaly, N.A. Abdel Hafez, E.A. Ragab, H.M. Awad, M.M. Abdalla, Eur. J. Med. Chem. 45, 492 (2010)

    Article  CAS  Google Scholar 

  13. P. Wang, S.-L. Lai, W. Liu, C.-S. Lee, S.-T. Lee, Z. Liu, Adv. Mater. 22, 527 (2010)

    Article  CAS  Google Scholar 

  14. S.-L. Lai, W. Liu, P. Wang, J. You, C.S. Lee, Z. Liu, J. Mater. Chem. 21, 12977 (2011)

    Article  Google Scholar 

  15. B.F. Abdel-Wahab, R.E. Khidre, A.A. Farahat, ARKIVOC (i), 196 (2011)

  16. B.F. Abdel-Wahab, R.E. Khidre, A.A. Farahat, A.-A.S. El-Ahl, ARKIVOC (i), 211 (2012)

  17. W.M. Abdou, R.E. Khidre, Curr. Org. Chem. 16, 913 (2012)

    Article  CAS  Google Scholar 

  18. R.E. Khidre, B.F. Abdel-Wahab, Curr. Org. Chem. 17(4), 430–445 (2013)

    Article  CAS  Google Scholar 

  19. R. E. Khidre, H. A, B. F. Abdel-Wahab, Turk. J. Chem. (2013, in press)

  20. H.-F. Wang, P. Li, H.-F. Cui, X.-W. Wang, J.-K. Zhang, W. Liu, G. Zhao, Tetrahedron 67, 1774 (2011)

    Article  CAS  Google Scholar 

  21. P. Li, Z. Chai, S.-L. Zhao, Y.-Q. Yang, H.-F. Wang, C.-W. Zheng, Y.-P. Cai, G. Zhao, S.-Z. Zhu, Chem. Commun. 47, 7369 (2009)

    Article  Google Scholar 

  22. V.G. Nenajdenko, S.V. Druzhinin, E.S. Balenkova, Mendeleev Commun. 3, 180 (2006)

    Article  Google Scholar 

  23. S.-L. Zhao, C.-W. Zheng, H.-F. Wang, G. Zhao, Adv. Synth. Cat. 351, 2811 (2009)

    Article  CAS  Google Scholar 

  24. C. Li, Q. Zhang, X. Tong, Chem. Commun. 46, 7828 (2010)

    Article  CAS  Google Scholar 

  25. F.M.A. El-Taweel, D.A. Ibrahim, M.A. Hanna, Boll. Chim. Farm. 140, 287 (2001)

    CAS  Google Scholar 

  26. M.E.A. Zaki, A.A. Fadda, K. Samir, F.A. Amer, Chem. Heterocycl. Compd. 39, 1242 (2003)

    Article  CAS  Google Scholar 

  27. A.-Z.A. Elassar, Y.M. Elkholy, Trends Org. Chem. 12, 53 (2008)

    CAS  Google Scholar 

  28. G. Heinisch, W. Holzer, G.A.M. Nawwar, Monatsh. Chem. 117, 247 (1986)

    Article  CAS  Google Scholar 

  29. F.M. Abdelrazek, Z.E.-S. Kandeel, K.M.H. Himly, M.H. Elnagdi, Synthesis 4, 432 (1985)

    Article  Google Scholar 

  30. N. Martin, A. Martinez-Grau, C. Seoane, J.L. Marco, Tetrahedron Asymmetry 6, 255 (1995)

    Google Scholar 

  31. U. Das, C.-H. Huang, W. Lin Chem, Commun. 48, 5590 (2012)

    CAS  Google Scholar 

  32. Q. Zhang, T. Fang, X. Tong, Tetrahedron 66, 8095 (2010)

    Article  CAS  Google Scholar 

  33. A. Palasz, T. Palasz, Tetrahedron 67, 1422 (2011)

    Article  CAS  Google Scholar 

  34. C.-P. Chuang, An-I Tsai, Tetrahedron 63, 9712 (2007)

    Article  CAS  Google Scholar 

  35. M.O. Kolosov, N.M. Kolos, N.Y. Gorobets, V.D. Orlov, Kharkov University Bull. 596, 60 (2003)

    CAS  Google Scholar 

  36. M.O. Kolosov, N.M. Kolos, N.Y. Gorobets, V.D. Orlov, Chem. Abstr. 144, 71369 (2006)

    Google Scholar 

  37. O.H. Hishmat, K.H.M. Khalil, F.M. Abdel Galil, S.I. El-Naem, A.A. Magd-l-Din, Pharmazie 44, 793 (1989)

    CAS  Google Scholar 

  38. A.K.M.N. Gohar, F.F. Abdel-Latif, M.S. El-Ktatny, Indian J. Chem. 26B, 274 (1987)

    CAS  Google Scholar 

  39. A.K.M.N. Gohar, F.F. Abdel-Latif, M.S. El-Ktatny, Chem. Abstr. 108, 55920 (1988)

    Google Scholar 

  40. K. Bogandowicz-Szwed, A. Palasz, Monatsh. Chem. 130, 795 (1999)

    CAS  Google Scholar 

  41. M. Mollazadeh, M.J. Khoshkholgh, S. Balalaie, F. Rominger, H.R. Bijanzadeh, J. Heterocycl. Chem. 47, 1200 (2010)

    Google Scholar 

  42. N.S. Ibrahim, M.H. Mohamed, M. Mahfouz, M.H. Elnagdi, J. Prakt. Chem. (Leipzig) 331, 375 (1989)

    Google Scholar 

  43. T. M. Abu Elmaati, S.B. Said, N.S. Abu Elenein, N.M. Khodeir, M.M. Sofan, J. Heterocycl. Chem. 40, 481 (2003)

    Google Scholar 

  44. R.A. Bunce, D. Rogers, T. Nago, S.A. Bryant, J. Heterocycl. Chem. 45, 547 (2008)

    Article  CAS  Google Scholar 

  45. G.E.H. Elgemeie, H.A. Elfahham, S. Elgamal, M.H. Elnagdi, Heterocycles 23, 1999 (1985)

    Article  CAS  Google Scholar 

  46. F.M. Abdelrazek, F.A. Michael, J. Heterocycl. Chem. 43, 7 (2006)

    Article  CAS  Google Scholar 

  47. R. Lisiak, J. Mlochowski, Synth. Commun. 39, 4271 (2009)

    Article  CAS  Google Scholar 

  48. X. Huang, R. Shen, Synthesis 16, 2731 (2006)

    Article  Google Scholar 

  49. N. Mizuyama, Y. Murakami, S. Kohra, K. Ueda, K. Hiraoka, J. Nagaoka, K. Takahashi, Y. Shigemitsu, Y. Tominaga, J. Heterocycl. Chem. 44, 115 (2007)

    Article  CAS  Google Scholar 

  50. S.M. Agamy, J. Chem. Res., Synop. 9, 349 (2001)

    Google Scholar 

  51. M.A. Al-Shiekh, H.Y. Medrassi, M.H. Elnagdi, E.A. Hafez, ARKIVOC (xvii), 36 (2008)

  52. M.R. Shaaban, T.S. Saleh, A.M. Farag, Heterocycles 78, 699 (2009)

    Article  CAS  Google Scholar 

  53. S.M. Sayed, M.A. Khalil, M.A. Ahmed, M.A. Raslan, Synth. Commun. 32, 481 (2002)

    Article  CAS  Google Scholar 

  54. K.M. Al-Zaydi, E.A. Hafez, M.H. Elnagdi, J. Chem. Res., Synop. 4, 154 (2000)

    Google Scholar 

  55. F. Al-Omran, O.Y.A. El-Hay, A.A. El-Khair, J. Heterocycl. Chem. 37, 1617 (2000)

    Article  CAS  Google Scholar 

  56. M.H. Elnagdi, F. Abdel Maksoud, A. Aal, E. Abdel Aziz Hafez, Y.M. Yassin, Z. Naturforsch., B: Chem. Sci. 44, 683 (1989)

    Google Scholar 

  57. H.H. Abdel-Razik, A.A. Fadda, Synth. Commun. 31, 3547 (2001)

    Article  CAS  Google Scholar 

  58. N.S. Ibrahim, K.U. Sadek, F.A. Abdel-Al, Arch. Pharm. 320, 240 (1987)

    Article  CAS  Google Scholar 

  59. S.A.S. Ghozlan, F.M. Abdelrazek, M.H. Mohamed, K.E. Azmy, J. Heterocycl. Chem. 47, 1379 (2010)

    Article  CAS  Google Scholar 

  60. D.V. Kryl’skii, KhS Shikhaliev, A.S. Chuvashlev, Russ. J. Org. Chem. 46, 410 (2010)

    Article  Google Scholar 

  61. M.A. Barsy, E.A. El-Rady, J. Heterocycl. Chem. 43, 523 (2006)

    Article  CAS  Google Scholar 

  62. F.M. Abdelrazek, A.M. Salah, Z.E. Elbazza, Arch. Pharm. 325, 301 (1992)

    Article  CAS  Google Scholar 

  63. R. Boehm, R. Pech, D. Lohmann, G. Laban, B. Petzold, Patent DD 234268 (1986). http://www.worldwide.espacenet.com/numberSearch?locale=en_EP

  64. A.O. Abdelhamid, B.Y. Riad, S.I. Aziz, Arch. Pharm. 320, 642 (1987)

    Article  CAS  Google Scholar 

  65. KhS Shikhaliev, V.I. Kryl’skaya, AYu. Potapov, Russ. Chem. Bull. 55, 1089 (2006)

    Article  CAS  Google Scholar 

  66. T.V. Hughes, S.L. Emanuel, A.K. Beck, S.K. Wetter, P.J. Connolly, P. Karnachi, M. Reuman, J. Seraj, A.R. Fuentes-Pesquera, R.H. Gruninger, S.A. Middleton, R. Lin, J.M. Davis, D.F.C. Moffat, Bioorg. Med. Chem. Lett. 17, 3266 (2007)

    Article  CAS  Google Scholar 

  67. M.A.M. Gad-Elkareem, A.M. Abdel-Fattah, M.A.A. Elneairy, Can. J. Chem. 85, 592 (2007)

    CAS  Google Scholar 

  68. F. Orvieto, D. Branca, C. Giomini, P. Jones, U. Koch, J.M. Ontoria, M.C. Palumbi, M. Rowley, C. Toniatti, E. Muraglia, Bioorg. Med. Chem. Lett. 19, 4196 (2009)

    Article  CAS  Google Scholar 

  69. T.D. Penning, S.A. Thomas, P.J. Hajduk, D.R. Sauer, K. Sarris, V.L. Giranda, WO 2007149907 (2007). http://www.worldwide.espacenet.com/numberSearch?locale=en_EP

  70. P. Jones, E. Muraglia, J.M. Ontoria, WO 2007144669 (2007). http://www.worldwide.espacenet.com/numberSearch?locale=en_EP

  71. T.E. Jr. Vasquez, T. Nixey, B. Chenera, V. Gore, M.D. Bartberger, Y. Sun, C. Hulme Mol. Diversity 7, 161 (2003)

  72. A.H.H. Elghandour, M.M.M. Ramiz, M.H. Elnagdi, Synthesis 10, 775 (1989)

    Article  Google Scholar 

  73. H.M. Al-Matar, K.D. Khalil, A.Y. Adam, M.H. Elnagdi, Molecules 15, 6619 (2010)

    Article  CAS  Google Scholar 

  74. A.Yu. Aizikovich, F.F. Zaripova, Zh. Org. Khim. 22, 1564 (1986); A.Yu. Aizikovich, F.F. Zaripova, Chem. Abstr. 106, 196379 (1987)

  75. S.K. Kotovskaya, S.A. Romanova, V.N. Charushin, O.N. Chupakhin, Russ. J. Org. Chem. 38, 1046 (2002)

    Article  CAS  Google Scholar 

  76. F.M. Abd El Latif, E.A. El Rady, M.A. Khalil, Phosphorus, Sulfur. Silicon Relat. Elem. 177, 2497 (2002)

    Article  CAS  Google Scholar 

  77. A.O. Abdelhamid, H.F. Zohdi, M.M. Ziada, Indian J. Chem. 40B, 284 (2001)

    CAS  Google Scholar 

  78. M.K.A. Ibrahim, M.M.M. Ramiz, A.H.H. El-Ghandour, J. Chem. Soc. Pak. 11, 291 (1989)

    CAS  Google Scholar 

  79. M.K.A. Ibrahim, M.M.M. Ramiz, A.H.H. El-Ghandour, Chem. Abstr. 113, 191303 (1990)

    Google Scholar 

  80. H.A. Elfahham, G.E.H. Elgemeie, Y.R. Ibraheim, M.H. Elnagdi, Liebigs Annalen Chem. 8, 819 (1988)

    Article  Google Scholar 

  81. M.M.M. Ramiz, A.H.H. Elghandour, M.K. Ibrahim, O.A.E.R. Mansour, Arch. Pharm. 322, 557 (1989)

    Article  CAS  Google Scholar 

  82. G.H. Elgemeie, A.H. Elghandour, H.M. Elshimy, J. Prakt. Chem. 331, 466 (1989)

    Article  CAS  Google Scholar 

  83. A.A. El-Agamey, M.R.H. Elmoghayar, M.H. Elnagdi, Pharmazie 40, 176 (1985)

    CAS  Google Scholar 

  84. S.A. Swelam, N.S. El-Said, A.S. Aly, A.M. Abdel-Fatth, Int. J. Pharm. Tech. Res. 1, 445 (2009)

    CAS  Google Scholar 

  85. A.O. Abdelhamid, M.A.M. Afifi, Sulfur Lett. 6, 125 (1987)

    CAS  Google Scholar 

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Authors and Affiliations

  1. Applied Organic Chemistry Department, National Research Centre, Dokki, 12622, Giza, Egypt

    Bakr F. Abdel-Wahab

  2. Preparatory Year, Shaqra University, Al-Dawadami, Saudi Arabia

    Bakr F. Abdel-Wahab

  3. Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI, 53201-1881, USA

    Mohamed F. El-Mansy

  4. Chemical Industries Division, National Research Centre, Dokki, 12622, Giza, Egypt

    Rizk E. Khidre

  5. Chemistry Department, Faculty of Science, Jazan University, Jazan, Saudi Arabia

    Rizk E. Khidre

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  1. Bakr F. Abdel-Wahab
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  3. Rizk E. Khidre
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Abdel-Wahab, B.F., El-Mansy, M.F. & Khidre, R.E. Production of pyrans, pyridazines, pyrimidines, pyrazines and triazine compounds using benzoylacetonitriles as a precursor. J IRAN CHEM SOC 10, 1085–1102 (2013). https://doi.org/10.1007/s13738-013-0244-2

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