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Chemistry of bicyclic [1,3,4]thiadiazole 5-5 systems containing ring-junction nitrogen

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Abstract

This review provides a survey of the advances in the methods of formation and chemical reactivity of bicyclic [1,3,4]thiadiazole 5-5 systems containing ring-junction nitrogen over the period from 1989 to the beginning of 2017.

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References

  1. A. Katritzky, C. Ramsden, E. Scriven, R. Taylor, in Comprehensive Heterocyclic Chemistry III, vol. 11, ed. by J. Marco-Contelles, E. Perez-Mayoral, P. Ballesteros (Elsevier Science, 2008), p. 199–303

  2. W.S. Hamama, M.A. Gouda, M.H. Abdelwahab, H.H. Zoorob, J. Heterocycl. Chem. 50, 787 (2013)

    Article  CAS  Google Scholar 

  3. F.A. Ragab, H.I. Heiba, M.G. El-Gazzar, S.M. Abou-Seri, W.A. El-Sabbaghb, R.M. El-Hazekb, Med. Chem. Commun. 7, 2309 (2016)

    Article  CAS  Google Scholar 

  4. H. Kaur, H.P. Kaur, P. Chawla, A. Chawla, U.S. Baghel, Am. J. Pharm. Tech. Res. 1, 213 (2011)

    Google Scholar 

  5. A.A. Karigar, M. Himaja, S.V. Mali, K.P. Jagadeesh, M.S. Sikarwar, IRJP 2, 153 (2011)

    Google Scholar 

  6. A.M. Khazi, A.K. Gadad, R.S. Lamani, B.A. Bhongade, Tetrahedron 67, 3289 (2011)

    Article  CAS  Google Scholar 

  7. J. Ramprasad, N. Nayak, U. Dalimba, P. Yogeeswari, D. Sriram, Med. Chem. Commun. 7, 338 (2016)

    Article  CAS  Google Scholar 

  8. J. Ramprasad, N. Nayak, U. Dalimba, P. Yogeeswari, D. Sriram, S.K. Peethambar, R. Achur, H.S. Kumar, Eur. J. Med. Chem. 95, 49 (2015)

    Article  CAS  Google Scholar 

  9. H.M. Patela, B. Singb, V. Bhardwajc, M. Palkara, M.S. Shaikha, R. Ranea, W.S. Alwana, A.K. Gadadd, M.N. Noolvie, R. Karpoormatha, Eur. J. Med. Chem. 93, 599 (2015)

    Article  Google Scholar 

  10. R.S. Jvarma, Hetero. Chem. 36, 1565 (1999)

    Article  Google Scholar 

  11. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles Structure, Reactions, Syntheses, and Applications, 2nd edn. (Wiley, Weinheim, 2003)

    Google Scholar 

  12. M. Kidwai, S. Rastogi, Lett. Org. Chem. 3, 149 (2006)

    Article  CAS  Google Scholar 

  13. J. Ramprasad, N. Nayak, U. Dalimba, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 25, 4169 (2015)

    Article  CAS  Google Scholar 

  14. M. Jag, G.S.R. Anjaneyulu Kiran. Indian J. Chem. 28A, 500 (1989)

    Google Scholar 

  15. M. Jag, V. Singh, V. Kumar, S. Kataria, Indian J. Chem. 33B, 692 (1994)

    Google Scholar 

  16. A.V. Ivashchenko, S.I. Torgova, L.A. Karamysheva, A.G. Abolin, Liq. Cryst. 7, 475 (1990)

    Article  CAS  Google Scholar 

  17. A. Scozzafava, C.T. Supuran, Met. Based Drugs 4, 19 (1997)

    Article  CAS  Google Scholar 

  18. S. Fajgelj, B. Stanovnik, M. Tisler, Heterocycles 24, 379 (1986)

    Article  CAS  Google Scholar 

  19. W.S. Alwan, R. Karpoormath, M.B. Palkar, H.M. Patel, R.A. Rane, M.S. Shaikh, A. Kajee, K.P. Mlisana, Eur. J. Med. Chem. 95, 514 (2015)

    Article  Google Scholar 

  20. B. Chaturvedi, N. Tiwari, A. Nizamuddin, Indian J. Chem. 28B, 358 (1989)

    CAS  Google Scholar 

  21. S.S. Shafi, T.R. Radhakrishnan, J. Indian, Heterocycl. Chem. 7, 231 (1998)

    CAS  Google Scholar 

  22. K.T. Potts, J.M. Kane, Synthesis 12, 1027 (1986)

    Article  Google Scholar 

  23. M.M. Kandeel, Bull. Pol. Acad. Sci. 50, 309 (2002)

    CAS  Google Scholar 

  24. N. Terzioglu, A. Gürsoy, Eur. J. Med. Chem. 38, 781 (2003)

    Article  CAS  Google Scholar 

  25. R. Leung-Toung, T.F. Tam, Y. Zhao, C.D. Simpson, W. Li, D. Desilets, K. Karimian, J. Org. Chem. 70, 6230 (2005)

    Article  CAS  Google Scholar 

  26. J. Mohan, Indian J. Chem. 38B, 867 (1999)

    CAS  Google Scholar 

  27. M. Himaja, A. Karigar, M.V. Ramana, D. Munirajasekhar, S.S. Mukesh, M. Himaja, M. Himaja, Lett. Drug Des. Discov. 9, 611 (2012)

    Article  CAS  Google Scholar 

  28. H.M. Abo-Salem, M.S. Ebaid, E.R. El-Sawy, A.E. El-Gendy, H.A. Mandour, Egypt Pharm. J. 12, 11 (2013)

    Google Scholar 

  29. H. Malipeddil, A.A. Karigar, V.R. Malipeddi, M.S. Sikarwar, Trop. J. Pharm. Res. 11, 611 (2012)

    Google Scholar 

  30. A.R. Saundane, Y. Manjunatha, P. Walmik, Heterocycl. Commun. 15, 303 (2009)

    Article  CAS  Google Scholar 

  31. A. Sing, A. Nizamuddin, S. Sharma, Indian J. Chem. 43B, 901 (2004)

    Google Scholar 

  32. L.D.S. Yadav, A. Vaish, S. Sharma, J. Agric. Food Chem. 42, 811 (1994)

    Article  CAS  Google Scholar 

  33. L.D.S. Yadav, S. Singh, Indian J. Chem. 40B, 440 (2001)

    CAS  Google Scholar 

  34. T.E. Ali, S.A. Abdel-Aziz, H.M. El-Shaaer, F.I. Hanafy, A.Z. El-Fauomy. Phosphorus Sulfur Silicon Relat. Elem. 183, 2139 (2008)

    Article  CAS  Google Scholar 

  35. S. Tiwari Nizamuddin. J. Indian Chem. Soc. 90, 679 (2013)

    Google Scholar 

  36. S.S. Shukurov, M.A. Kukaniev, A.M. Alibaeva, Russ. Chem. Bull. 45, 724 (1996)

    Article  Google Scholar 

  37. N. Tiwari, J. Indian Chem. Soc. 68, 144 (1991)

    CAS  Google Scholar 

  38. K. Singh, N. Tiwari, N. Nizamuddin, Indian J. Chem. 1993, 32B (1086)

    Google Scholar 

  39. T. Siddiqui, M.G. Alam, Chin. J. Chem. 26, 1339 (2008)

    Article  Google Scholar 

  40. T.S. Shamsuzzaman, G.A. Mohd, Indian J. Chem. 51B, 370 (2012)

    CAS  Google Scholar 

  41. M.A. Kukaniev, M.M. Akbarova, Z.G. Sangov, S.S. Safarov, D.M. Osimov, Chem. Heterocycl. Compd. 46, 605 (2010)

    Article  CAS  Google Scholar 

  42. V.N. Yarovenko, A.S. Nikitina, I.V. Zavarzin, M.M. Krayushkin, L.V. Kovalenko, Russ. J. Org. Chem. 43, 1364 (2007)

    Article  CAS  Google Scholar 

  43. E.K. Mikitenko, A.D. Kachkovskii, N.N. Romanov, Heterocycl. Compd. 8, 356–368 (1982)

    Google Scholar 

  44. E.K. Mikitenko, A.D. Kachkovskii, N.N. Romanov, Khim Soedinen ii 4, 484 (1982)

    Google Scholar 

  45. E.K. Mikitenko, N.N. Romanov, Chem. Heterocycl. Compd. 17, 141 (1981)

    Article  Google Scholar 

  46. M.M. Kochhar, M. Salahi-Asbahi, B.B. Williams, J. Pharm. Sci. 62, 336 (1973)

    Article  CAS  Google Scholar 

  47. E.K. Mikitenko, N.N. Romananov, Ukr. Khem. Zh. 47, 295 (1981)

    CAS  Google Scholar 

  48. E.K. Mikitenko, N.N. Romananov, Chem. Abst. 1981(94), 210279 (1981)

    Google Scholar 

  49. M.A. Eldawy, S.A. Shams El-Dine, K.M. El-Brembaly, Pharmazie 34, 248 (1979)

    CAS  Google Scholar 

  50. P. Molina, A. Arques, A. Alias, Tetrahedron 48, 1285 (1992)

    Article  CAS  Google Scholar 

  51. J. Mohan, Ind. J. Heterocycl. Chem. 12, 167 (2002)

    CAS  Google Scholar 

  52. G. Labbe, J. Buelenes, W.A. Dehean, J. Chem. Soc. Perkin Trans. 1, 1825 (1993)

    Article  Google Scholar 

  53. K. Hagiwara, K. Saitoh, T. Iimaha, T. Kawana, H. Hosaka, J. Pestic. Sci. 18, 309 (1993)

    Article  CAS  Google Scholar 

  54. D.P. Singh, S. Pratap, R.J. Butcher, S.K. Gupta, J. Chem. Crystallogr. 44, 115–122 (2014)

    Article  CAS  Google Scholar 

  55. F. Téllez, A. Cruz, H. López-Sandoval, I. Ramos-García, M. Gayosso, R. N. Castillo-Sierra, B. Paz-Michel, H. Nöth, A. Flores-Parra, R. Contreras, Eur. J. Org. Chem. 2004(20), 4203–4214 (2004)

    Article  Google Scholar 

  56. K. Ohkata, M. Ohsugi, K. Yamamoto, M. Ohsawa, K. Akiba, J. Am. Chem. Soc. 118, 6355 (1996)

    Article  CAS  Google Scholar 

  57. A. Castro, A. Martınez, J. Heterocycl. Chem. 36, 991 (1999)

    Article  CAS  Google Scholar 

  58. K.T. Potts, J.M.J. Kane, Heterocycl. Chem. 26, 1289 (1989)

    Article  CAS  Google Scholar 

  59. R.H. Khan, R.C. Rastogi, Indian J. Chem. 27B, 501 (1988)

    CAS  Google Scholar 

  60. E.A. Bakhite, ShM Radwan, Pharmazie 54, 491 (1999)

    CAS  Google Scholar 

  61. J.O. Gardner, C.C. Beard, J. Pharm. Sci. 68, 182 (1979)

    Article  CAS  Google Scholar 

  62. Y. Tanabe, A. Kawai, Y. Yoshida, M. Ogura, H. Okumura, Heterocycles 45, 1579 (1997)

    Article  CAS  Google Scholar 

  63. R.K. Bansal, R. Mahnot, D.C. Sharma, K. Karaghiosoxf, Synthesis 3, 267 (1992)

    Article  Google Scholar 

  64. W. Betzl, C. Hettstedt, K. Karaghiosoff, New J. Chem. 37, 481 (2013)

    Article  CAS  Google Scholar 

  65. K. Karaghiosoff, C. Cleve, A. Schmidpeter, R. Mahnot, N. Gandhi, R.K. Bansal, Chem. Ber. 128, 581 (1995)

    Article  CAS  Google Scholar 

  66. T. Pyl, F. Wasehk, H. Beyer. Justus Liebigs Ann. Chem. 663, 113 (1963)

    Article  CAS  Google Scholar 

  67. T. Pyl, F. Wasehk, H. Beyer. Justus Liebigs Chem. Abstr. 59, 5160d (1963)

    Google Scholar 

  68. B. Shi, Z. Zhu, Y.S. Zhu, D. Zhou, J. Wang, P. Zhoua, H. Jing, Org. Biomol. Chem. 14, 2978 (2016)

    Article  CAS  Google Scholar 

  69. T. Matsukawa, S. Ban, K. Shirakawa, M. Yoneda, Yakugaku Zasshi 73, 159 (1953)

    Article  CAS  Google Scholar 

  70. G.D. Kolavi, V.S. Hegde, I.M. Khazi, P. Gadad, Bioorg. Med. Chem. 14, 3069 (2006)

    Article  CAS  Google Scholar 

  71. A.V. Ivashchenko, O.S. Petrova, V.V. Titov, Mol. Cryst. Liq. Cryst. 145, 25 (1987)

    Article  CAS  Google Scholar 

  72. A.K. Gadad, C.S. Mahajanshetti, S. Nimbalkar, A. Raichurkar, Eur. J. Med. Chem. 35, 853 (2000)

    Article  CAS  Google Scholar 

  73. G.D. Kolavi, V.S. Hegde, I.M. Khazi, Synth. Commun. 2006, 36 (1837)

    Google Scholar 

  74. G. Kolavi, V. Hegde, I.A. Khazi, Tetrahedron Lett. 47, 2811 (2006)

    Article  CAS  Google Scholar 

  75. R. Leung-Toung, T.F. Tam, J.M. Wodzinska, Y. Zhao, J. Lowrie, C.D. Simpson, K. Karimian, M. Spino, J. Med. Chem. 48, 2266 (2005)

    Article  CAS  Google Scholar 

  76. V. Segarra, M.I. Crespo, F. Pujol, J. Beleta, T. Dome´nech, M. Miralpeix, J.M. Palacios, A. Castro, A. Martınez, Bioorg. Med. Chem. Lett. 8, 505 (1998)

    Article  CAS  Google Scholar 

  77. M. Himaja, A. Karigar, M.V. Ramana, D. Munirajasekhar, S.S. Mukesh, Lett. Drug Des. Discov. 9, 611 (2016)

    Article  Google Scholar 

  78. W.S. Hamama, M.E. Ibrahim, H.A. Raoof, H.H. Zoorob, J. Heterocycl. Chem. (2016). doi:10.1002/jhet.2826

    Google Scholar 

  79. R.K. Bansal, K. Karaghiosoff, N. Gupta, V. Kabra, R. Mahnot, D.C. Sharma, R. Munjal, S.K. Kumawat, Z. Naturforsch. Teil B 60, 7 (2005)

    CAS  Google Scholar 

  80. G.S. Gadaginamath, R.R. Kavali, A.S. Shyadligeri, H.P. Doddamani. Indian J. Heterocycl. Chem. 9, 33 (1999)

    CAS  Google Scholar 

  81. B.A. Bhongade, S. Talath, R.A. Gadad, A.K.J. Gadad, Saudi Chem. Soc. 20, S463 (2016)

    Article  CAS  Google Scholar 

  82. A. Katiyari, B. Metikurki, S. Prafullai, S. Kumar, S. Kushwaha, D. Schols, E. De clercq, S.S. Karkii, Acta Pol. Pharm. Drug Res. 73, 937 (2016)

    Google Scholar 

  83. J. Matysiak, A. Niewiadomy, Mol Divers. 21, 211 (2017)

    Article  CAS  Google Scholar 

  84. D.E. Abdel Rahman, K.O. Mohamed, Der Pharm. Chem. 6, 323 (2014)

    Google Scholar 

  85. V.K. Bhovi, Y.D. Bodke, Curr. Chem. Biol. 4, 145 (2016)

    Google Scholar 

  86. B.F. Abdel-Wahab, S. Shaaban, Synthesis 46, 1709 (2014)

    Article  Google Scholar 

  87. M. Himaja, A. Karigar, M.V. Ramana, D. Munirajasekhar, M.S. Sikarwar, Lett. Drug Des. Discov. 9, 611 (2012)

    Article  CAS  Google Scholar 

  88. T. Yokoi, S. Minami, Y. Nakagawa, H. Miyagawa, Pest. Biochem. Physiol. 120, 40 (2015)

    Article  CAS  Google Scholar 

  89. A.W.T. Bristow, T.J. Bumfrey, Chromatographia 55, 321 (2002)

    Article  CAS  Google Scholar 

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Acknowledgement

Financial support by the Faculty of Science, Mansoura University (Mansoura, Egypt) is gratefully appreciated.

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  1. Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, 35516, Egypt

    Wafaa S. Hamama, Mona E. Ibrahim, Hadeer A. Raoof & Hanafi H. Zoorob

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Hamama, W.S., Ibrahim, M.E., Raoof, H.A. et al. Chemistry of bicyclic [1,3,4]thiadiazole 5-5 systems containing ring-junction nitrogen. Res Chem Intermed 43, 6259–6291 (2017). https://doi.org/10.1007/s11164-017-2988-2

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