Skip to main content
SpringerLink
Log in

Synthesis of tetrazole and its derivatives by heterocyclization reaction involving primary amines, orthoesters, and azides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This review provides comprehensive analysis of literature data on the heterocyclization reaction of primary amines, orthoesters, and azides, which can be used for the preparation of tetrazole, its 1-mono- and 1,5-disubstituted derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1.
Scheme 2.
Scheme 3.
Scheme 4.
Scheme 5.
Scheme 6.
Scheme 7.
Scheme 8.
Scheme 9.
Scheme 10.
Figure 1.
Scheme 11.
Scheme 12.
Scheme 13.
Scheme 14.
Scheme 15.
Figure 2.
Scheme 16.
Scheme 17.
Scheme 18.
Figure 3.
Scheme 19.
Scheme 20.
Scheme 21.
Figure 4.
Scheme 22.
Scheme 23.
Scheme 24.
Scheme 25.
Scheme 26.
Scheme 27.

Similar content being viewed by others

References

  1. (a) He, P.; Zhang, J.-G.; Yin, X.; Wu, J.-T.; Wu, L.; Zhou, Z.-N.; Zhang, T.-L. Chem.–Eur. J. 2016, 22, 7670. (b) Klapötke, T. M. Chemistry of High-Energy Materials; Walter de Gruyter: Berlin, 2012, 2nd ed., p. 273. (c) Gao, H.; Shreeve, J. M. Chem. Rev. 2011, 111, 7377. (d) Singh, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Angew. Chem., Int. Ed. 2006, 45, 3584. (e) Gao, H.; Shreeve, J. M. Chem. Rev. 2011, 111, 7377.

  2. (a) Ostrovskii, V. A.; Koldobskii, G. I.; Trifonov, R. E. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008, Vol. 6, p. 257. (b) Ostrovskii, V. A.; Pevzner, M. S.; Kofman, T. P.; Shcherbinin, M. B.; Tselinskii, I. V. Targets Heterocycl. Syst. 1999, 3, 467.

  3. Trifonov, R. E.; Ostrovskii, V. A. Russ. J. Org. Chem. 2006, 42, 1599. [Zh. Org. Khim. 2006, 42, 1585.]

  4. Gaponik, P. N.; Voitekhovich, S. V.; Ivashkevich, O. A. Russ. Chem. Rev. 2006, 75, 507. [Usp. Khim. 2006, 75, 569.]

  5. Voitekhovich, S. V.; Gaponik, P. N.; Ivashkevich, O. A. Russ. Chem. Rev. 2002, 71, 721. [Usp. Khim. 2002, 71, 818.]

  6. Zhang, Q.; Shreeve, J. M. Chem. Rev. 2014, 114, 10527.

    Article  CAS  Google Scholar 

  7. Kamiya, T.; Saito, Y. JP Patent 7247031; Сhem. Аbstr. 1973, 78, 111331.

    Google Scholar 

  8. (a) Kamiya, T.; Saito, Y. US Patent 3767667; Сhem. Аbstr. 1974, 80, 27262a. (b) Kamiya, T.; Saito, Y. DE Patent 2147023; Сhem. Аbstr. 1973, 79, 5346. (c) Kamiya, T.; Saito, Y. FR Patent 2153772; Сhem. Аbstr. 1973, 79, 78807u.

  9. (a) Bison, G.; Heinzelmann, W.; Linkat, N. DE Patent 2348802; Сhem. Аbstr. 1975, 83, 58836. (b) Bison, G.; Linkat, N.; Wolfes, W. DE Patent 2854015; Сhem. Аbstr. 1981, 94, 15739n. (c) Janda, L.; Martvon, A. CZ Patent 259379; Сhem. Аbstr. 1989, 111, 134166.

  10. (a) Gaponik, P. N. Dissert. of Doctor of Chemical Sciences; Minsk, 2000. (b) Grigor'ev, Yu. V. Dissert. of Candidate of Chemical Sciences; St.Petersburg, 1998. (с) Voitekhovich, S. V.; Ivashkevich, O. A.; Gaponik, P. N. Russ. J. Org. Chem. 2013, 49, 635. [Zh. Org. Khim. 2013, 49, 655.]

  11. Butler, R. N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, New York, 1996, Vol. 4, p. 621.

  12. Gaponik, P. N.; Karavai V. P. Vestn. Belorus. Un-ta. Ser. 2 1980, Vol. 3, 51.

  13. Thomann, A.; Eberhard, J.; Allegretta, G.; Empting, M.; Hartmann, R. W. Synlett 2015, 26, 2606.

    Article  CAS  Google Scholar 

  14. Wang, X.; Liu, J.; Wang, D.; Bi, X.; Zhao, W. Z. Anorg. Allg. Chem. 2015, 641, 631.

    Article  CAS  Google Scholar 

  15. Klapötke, T. M.; Stein, M.; Stierstorfer, J. Z. Z. Anorg. Allg. Chem. 2008, 634, 1711.

    Article  Google Scholar 

  16. Bronisz, R. Inorg. Chim. Acta 2002, 340, 215.

    Article  CAS  Google Scholar 

  17. Grigor’ev, Yu. V.; Maruda, I. I.; Gaponik, P. N. Izv. NAN Belarusi 1997, Ser. 4, 80.

  18. Gaponik, P. N.; Karavai, V. P.; Grigor'ev, Yu. V. Chem. Heterocycl. Compd. 1985, 21, 1255. [Khim. Geterotsikl. Soedin. 1985, 1521.]

  19. Hassan, N.; Weinberger, P.; Mereiter, K.; Werner, F.; Molnar, G.; Bousseksou, A.; Valtiner, M.; Linert, W. Inorg. Chim. Acta 2008, 361, 1291.

    Article  CAS  Google Scholar 

  20. Hassan, N.; Stelzl, J.; Weinberger, P.; Molnar, G.; Bousseksou, A.; Kubel, F.; Mereiter, K.; Boca, R.; Linert, W. Inorg. Chim. Acta 2013, 396, 92.

    Article  CAS  Google Scholar 

  21. Voitekhovich, S. V.; Vorob'ev A. N.; Gaponik, P. N.; Ivashkevich, O. A. Chem. Heterocycl. Compd. 2005, 41, 999. [Khim. Geterotsikl. Soedin. 2005, 1174.]

  22. (a) Soliman, A. A.; Khattab, M. M.; Reissner, M.; Weinberger, P.; Werner, F.; Linert, W. Inorg. Chim. Acta 2007, 360, 3987. (b) Soliman, A. A.; Khattab, M. M.; Linert, W. J. Coord. Chem. 2005, 58, 421.

  23. Degtyarik, M. M.; Lyakhov A. S.; Ivashkevich, L. S.; Matulis, Vitaly E.; Matulis, Vadim E.; Gruschinski, S.; Voitekhovich, S. V.; Kersting, B.; Ivashkevich, O. A. Dalton Trans. 2015, 44, 18518.

  24. Hassan, N.; Weinberger, P.; Kubel, F.; Molnar, G.; Bousseksou, A.; Dlhan, L.; Boca, R.; Linert, W. Inorg. Chim. Acta 2009, 362, 3629.

    Article  CAS  Google Scholar 

  25. Satoh, Y.; Marcopulos, N. Tetrahedron Lett. 1995, 36, 1759.

    Article  CAS  Google Scholar 

  26. Wiedemann, S. H.; Bio, Matthew M.; Brown, L. M.; Hansen, K. B.; Langille, N. F. Synlett 2012, 23, 2231.

    Article  CAS  Google Scholar 

  27. Tafili-Kryeziu, M.; Caneschi, A.; Fittipaldi, M.; Spina, G.; Lantieri, M.; Weil, M.; Hasegawa, M.; Linert, W. J. Coord. Chem. 2015, 68, 3457.

    Article  CAS  Google Scholar 

  28. Stokker, G. E.; Deana, A. A.; deSolms, S. J.; Schultz, E. M.; Smith, R. L.; Cragoe, E. J., Jr.; Baer, J. E.; Russo, H. F.; Watson L. S. J. Med. Chem. 1982, 25; 735.

  29. Gaponik, P. N.; Karavai, V. P. Chem. Heterocycl. Compd. 1985, 21, 1172. [Khim. Geterotsikl. Soedin. 1985, 1422.]

  30. Stassen, A. F.; Grunert, M.; Mills, A. M.; Spek, A. L.; Haasnoot, J. G.; Reedijk, J.; Linert, W. Dalton Trans. 2003, 3628.

  31. Putis, S. M.; Shuvalova, E. S.; Ostrovskii, V. A. ARKIVOC 2009, (4), 64.

    Google Scholar 

  32. (a) Stassen, A. F.; Kooijman, H.; Spek, A. L.; Haasnoot, J. G.; Reedijk, J. J. Chem. Cryst. 2001, 31, 307. (b) Stassen, A. F.; Dova, E.; Ensling, J.; Schenk, H.; Gutlich, P.; Haasnoot, J. G.; Reedijk, J. Inorg. Chim. Acta 2002, 335, 61.

  33. Stassen, A. F.; Grunert, M.; Dova, E.; Müller, M.; Weinberger, P.; Linert, W.; Haasnoot, J. G.; Reedijk, J. Eur. J. Inorg. Chem. 2003; 2273.

  34. Bialonska, A.; Bronisz, R. Tetrahedron 2008, 64, 9771.

    Article  CAS  Google Scholar 

  35. Muttenthaler, M.; Bartel, M.; Weinberger, P.; Hilscher, G.; Linert, W. J. Mol. Struct. 2005, 741, 159.

    Article  CAS  Google Scholar 

  36. Polyakova, I. N.; Saraev, V. V.; Gavrilov, A. S.; Golod, E. L. Crystallogr. Repts. 2009, 54, 441. [Kristallografiya 2009, 54, 475.]

  37. Andreeva, T. N.; Lyakhov, A. S.; Ivashkevich, L. S.; Voitekhovich, S. V.; Grigoriev, Y. V.; Ivashkevich, O. A. Z. Anorg. Allg. Chem. 2015, 641, 2312.

    Article  CAS  Google Scholar 

  38. Grigor'ev, Yu. V.; Voitekhovich, S. V.; Lyakhov, A. S.; Ivashkevich, L. S.; Buglak, A. F.; Ivashkevich, O. A. Russ. J. Org. Chem. 2014, 50, 742. [Zh. Org. Khim. 2014, 50, 752.]

  39. Vorob'ev, A. N.; Gaponik, P. N.; Petrov, P. T. Izv. NAN Belarusi 2003, Iss. 2, 50.

  40. Gaponik, P. N.; Karavai, V. P.; Davshko, I. E.; Degtyarik, M. M.; Bogatikov, A. N. Chem. Heterocycl. Compd. 1990, 26, 1274. [Khim. Geterotsikl. Soedin. 1990, 1528.]

  41. Ichikawa, T.; Kitazaki, T.; Matsushita, Y.; Hosono, H.; Yamada, M.; Mizuno, M.; Itoh, K. Chem. Pharm. Bull. 2000, 48, 1947.

    Article  CAS  Google Scholar 

  42. Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, M. D. Russ. J. Org. Chem. 2010, 46, 556. [Zh. Org. Khim. 2010, 46, 565.]

  43. Vembu, S.; Pazhamalai, S.; Gopalakrishnan, M. Med. Chem. Res. 2016, 25, 1916.

    Article  CAS  Google Scholar 

  44. Velikorodov, A. V.; Stepkina, N. N.; Ionova, V. A.; Melent'eva E. A. Russ. J. Org. Chem. 2014, 50, 1184. [Zh. Org. Khim. 2014, 50, 1201.]

  45. Smith, L. M.; Orwat, M. J.; Hu, Z.; Han, W.; Wang, C.; Rossi, K. A.; Gilligan, P. J.; Pabbisetty, K. B.; Osuna, H.; Corte, J. R.; Rendina, A. R.; Luettgen, J. M.; Wong, P. C.; Narayanan, R.; Harper, T. W.; Bozarth, J. M.; Crain, E. J.; Wei, A.; Ramamurthy, V.; Morin, P. E.; Xin, B.; Zheng, J.; Seiffert, D. A.; Quan, M. L.; Lam, P. Y. S.; Wexler, R. R.; Pinto, D. J. P. Bioorg. Med. Chem. Lett. 2016, 26, 472.

    Article  CAS  Google Scholar 

  46. Cable, K. M.; Wells, G. N.; Sutherland, D. R. J. Labelled Compd. Radiopharm. 2000, 43; 29.

    Article  CAS  Google Scholar 

  47. Romagnoli, R.; Baraldi, P. G.; Salvador, M. K.; Preti, D.; Aghazadeh Tabrizi, M.; Brancale, A.; Fu, X.-H.; Li, J.; Zhang, S.-Z.; Hamel, E.; Bortolozzi, R.; Basso, G.; Viola, G. J. Med. Chem. 2012, 55, 475.

    Article  CAS  Google Scholar 

  48. Grunert, C. M.; Weinberger, P.; Schweifer, J.; Hampel, C.; Stassen, A. F.; Mereiter, K.; Linert, W. J. Mol. Struct. 2005, 733, 41.

    Article  CAS  Google Scholar 

  49. Voitekhovich, S. V.; Gaponik, P. N.; Lyakhov, A. S.; Ivashkevich, O. A. Polish J. Chem. 2001, 75, 253.

    CAS  Google Scholar 

  50. Howard, N.; Abell, C.; Blakemore, W.; Chessari, G.; Congreve, M.; Howard, S.; Jhoti, H.; Murray, C. W.; Seavers, L. C. A.; Van Montfort, R. L. M. J. Med. Chem. 2006, 49, 1346.

    Article  CAS  Google Scholar 

  51. Scott, J. S.; Bowker, S. S.; Brocklehurst, K. J.; Brown, H. S.; Clarke, D. S.; Easter, A.; Ertan, A.; Goldberg, K.; Hudson, J. A.; Kavanagh, S.; Laber, D.; Leach, A. G.; Macfaul, P. A.; Martin, E. A.; McKerrecher, D.; Schofield, P.; Svensson, P. H.; Teague, J. J. Med. Chem. 2015, 57, 8984.

    Article  Google Scholar 

  52. Mochida, T.; Shimizu, H.; Suzuki, S.; Akasaka, T. J. Organomet. Chem. 2006, 691, 4882.

  53. Ostrovskii, V. A.; Mazur, M. S.; Mikhailenko, V. V.; Aksenov, N. A.; Aksenov, A. V. Chem. Heterocycl. Compd. 2016, 52, 849. [Khim. Geterotsikl. Soedin. 2016, 52, 849.]

  54. Mezheritskii, V. V.; Olekhnovich, E. P. Dorofeenko, G. N. Russ. Chem. Rev. 1973, 42, 392. [Usp. Khim. 1973, 42, 896.]

  55. Gaponik, P. N.; Grigor'ev, Yu. V.; Karavai, V. P. Chem. Heterocycl. Compd. 1985, 21, 477. [Khim. Geterotsikl. Soedin. 1985, 566.]

  56. Vorob'ev, A. N.; Baranovskii, A. V.; Gaponic, P. N.; Ivashkevich, O. A. Russ. J. Org. Chem. 2010, 46, 291. [Zh. Org. Khim. 2010, 46, 295.]

  57. Koningsbruggen, P. J.; Garcia, Y.; Bravic, G.; Chasseau, D.; Kahn, O. Inorg. Chim. Acta 2001, 326, 101.

    Article  Google Scholar 

  58. Quesada, M.; Kooijman, H.; Gamez, P.; Sanchez Costa, J.; Van Koningsbruggen, P. J.; Weinberger, P.; Reissner, M.; Spek, A. L.; Haasnoot, J. G.; Reedijk, J. Dalton Trans. 2007, 5434.

  59. Werner, F.; Mereiter, K.; Tokuno, K.; Inagaki, Y.; Hasegawa, M. Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o2726.

    Article  Google Scholar 

  60. Quesada, M.; Prins, F.; Roubeau, O.; Gamez, P.; Teat, S. J.; Van Koningsbruggen, P. J.; Haasnoot, J. G.; Reedijk, J. Inorg. Chim. Acta 2007, 360, 3787.

    Article  CAS  Google Scholar 

  61. Van Koningsbruggen, P. J.; Garcia, Y.; Kooijman, H.; Spek, A. L.; Haasnoot, J. G.; Kahn, O.; Linares, J.; Codjovi, E.; Varret, F. J. Chem. Soc., Dalton Trans. 2001, 466.

  62. Absmeier, A.; Bartel, M.; Carbonera, C.; Jameson, G. N. L.; Weinberger, P.; Caneschi, A.; Mereiter, K.; Letard, J.-F.; Linert, W. Chem.–Eur. J. 2006, 12, 2235.

  63. Quesada, M.; Prins, F.; Bill, E.; Kooijman, H.; Gamez, P.; Roubeau, O.; Spek, A.; L.; Haasnoot, J. G.; Reedijk, J. Chem.–Eur. J. 2008, 14, 8486.

  64. Gaponik, P. N.; Voitekhovich, S. V.; Maruda, I. I.; Kulak, A. A.; Ivashkevich, O. A. Izv. NAN Belarusi 2001, (3), 62.

  65. Coronado, E.; Gimenez-Marques, M.; Minguez Espallargas, G.; Rey, F.; Vitorica-Yrezabal, I. J. J. Am. Chem. Soc. 2013, 135, 15986.

    Article  CAS  Google Scholar 

  66. Pazik, A.; Skwierawska, A. J. Inclusion Phenom. Macrocyclic Chem. 2013, 77, 83

    Article  CAS  Google Scholar 

  67. Voitekhovich, S. V.; Grigoriev, Yu. V.; Lyakhov, A. S.; Ivashkevich, L. S.; Ivashkevich, O. A. Dalton Trans. 2016, 45, 13406.

  68. Boland, Y.; Safin, D. A.; Tinant, B.; Babashkina, M. G.; Marchand-Brynaert, J.; Garcia, Y. New J. Chem. 2013, 37, 1174.

    CAS  Google Scholar 

  69. Hartdegen, V.; Klapötke, T. M.; Sproll, S. M. Z. Naturforsch., B: J. Chem. Sci. 2009, 64b, 1535.

    Google Scholar 

  70. Litkei, G.; Patonay, T.; Patonai-Peli, E.; Khiliya, V. P. Pharmazie 1989, 44, 791.

    CAS  Google Scholar 

  71. Azad, C. S.; Narula, A. K. RSC Adv. 2016, 6, 19052.

    Article  CAS  Google Scholar 

  72. Shanmugam, G.; Bhakiaraj, D.; Elavarasan, S.; Elavarasan, T.; Gopalakrishnan, M. Chem. Sci. Trans. 2013, 2, 1304.

    Google Scholar 

  73. Boland, Y.; Hertsens, P.; Marchand-Brynaert, J.; Garcia, Y. Synthesis 2006, 1504.

  74. Lyakhov, A. S.; Grigoriev, Y. V.; Ivashkevich, L. S.; Gaponik, P. N. Acta Crystallogr., Sect. E: Struct. Rep. Online 2007, E63, m495.

  75. Habibi, D.; Rahmani, P.; Ahmadi, F.; Bokharaei, H.; Kaboudvand, Z. Lett. Org. Chem. 2014, 11, 145

    Article  CAS  Google Scholar 

  76. Voitekhovich, S. V.; Grigor'ev, Yu. V.; Gaponik, P. N.; Ivashkevich O. A. Vestn. Belorus. Un-ta. Ser. 2. 2010, Vol. 3, 11.

  77. Chuprun, S. S.; Popova, E. A.; Mukhametshina, A. V.; Trifonov, R. E. Russ. J. Org. Chem. 2015, 51, 1671. [Zh. Org. Khim. 2015, 51, 1700.]

  78. Fischer, N.; Izsák, D.; Klapötke, T. M.; Stierstorfer, J. Chem.– Eur. J. 2013, 19, 8948.

  79. Srinivas, D.; Ghuleb, V. D.; Muralidharan, K. RSC Adv. 2014, 4, 7041

    Article  CAS  Google Scholar 

  80. Pagacz-Kostrzewa, M.; Reva, I. D.; Bronisz, R.; Giuliano, B. M.; Fausto, R.; Wierzejewska, M. J. Phys. Chem. A 2011, 115, 5693.

    Article  CAS  Google Scholar 

  81. Sinditskii, V. P.; Dutov, M. D.; Fogelzang, A. E.; Vernidub, T. Y.; Sokol, V. I.; Porai-Koshits, M. A. Inorg. Chim. Acta 1991, 189, 259.

    Article  CAS  Google Scholar 

  82. Vatsadze, I. A.; Serushkina, O. V.; Dutov, M. D.; Shkineva, T. K.; Suponitsky, K. Yu.; Ugrak B. I.; Dalinger, I. L. Chem. Heterocycl. Compd. 2015, 51, 695. [Khim. Geterotsikl. Soedin. 2015, 51, 695.]

  83. Pokhodylo, N. T.; Matiychuk V. S.; Obushak M. D. Chem. Heterocycl. Compd. 2010, 46, 140. [Khim. Geterotsikl. Soedin. 2010, 173.]

  84. Pokhodylo, N. T.; Matiychuk V. S.; Obushak, M. D. Tetrahedron 2008, 64, 1430.

    Article  CAS  Google Scholar 

  85. Abu-Hashem, A. A.; Abu-Zied, K. M.; El-Shehry, M. F. Monatsh. Chem. 2011, 142, 539.

    Article  CAS  Google Scholar 

  86. Pokhodylo, N. T.; Shyyka, O. Y.; Matiychuk, V. S.; Obushak, M. D. ACS Comb. Sci. 2015, 17, 399.

    Article  CAS  Google Scholar 

  87. Soares, M. I. L.; de Lyra, A. C. F.; Henriques, M. S. C.; Paixão, J. A.; Pinho e Melo, T. M. V. D. Tetrahedron 2015, 71, 3343.

    CAS  Google Scholar 

  88. Downard, A. J.; Steel, P. J.; Steenwijk, J. Aust. J. Chem. 1995, 48, 1625.

    Article  CAS  Google Scholar 

  89. Denton, T. T.; Zhang, X.; Cashman, J. R. J. Med. Chem. 2005, 48, 224.

    Article  CAS  Google Scholar 

  90. Gaponik, P. N.; Karavai, V. P. Chem. Heterocycl. Compd. 1983, 19, 681. [Khim. Geterotsikl. Soedin. 1983, 841.]

  91. Aridoss, G.; Laali, K. K. Eur. J. Org. Chem. 2011, 2827.

  92. Zarchi, M. A. K.; Nazem, F. J. Iran. Chem. Soc. 2014, 11, 91.

    Article  Google Scholar 

  93. Potewar, T. M.; Siddiqui, S. A.; Lahoti, R. J.; Srinivasan, K. V. Tetrahedron Lett. 2007, 48, 1721.

    Article  CAS  Google Scholar 

  94. Dighe, S. N.; Jain, K. S.; Srinivasan, K. V. Tetrahedron Lett. 2009, 50, 6139.

    Article  CAS  Google Scholar 

  95. Kundu, D.; Majee, A.; Hajra, A. Tetrahedron Lett. 2009, 50, 2668.

    Article  CAS  Google Scholar 

  96. Su, W.-K.; Hong, Z.; Shan, W.-G.; Zhang, X.-X. Eur. J. Org. Chem. 2006, 2723.

  97. Mittapalli, G. K.; Zhao, F.; Jackson, A.; Gao, H.; Lee, H.; Chow, S.; Kaur, M. P.; Nguyen, N.; Zamboni, R; McKelvy, J.; Wong-Staal, F.; Macdonald, J. E. Bioorg. Med. Chem. Lett. 2012, 22, 4955.

    Article  CAS  Google Scholar 

  98. Dorababu, A.; Kamble, R. R.; Kattimani, P. P. Lett. Org. Chem. 2013, 10, 510.

    Article  CAS  Google Scholar 

  99. Naeimi, H.; Mohamadabadi, S. Dalton Trans. 2014, 43, 12967.

    Article  CAS  Google Scholar 

  100. Habibi, D.; Nasrollahzadeh, M.; Kamali, T. A. Green Chem. 2011, 13, 3499.

    Article  CAS  Google Scholar 

  101. Khalafi-Nezhad, A.; Mohammadi, S. RSC Adv. 2013, 3, 4362.

    Article  CAS  Google Scholar 

  102. Dehghani, F.; Sardarian, A. R.; Esmaeilpour, M. J. Organomet. Chem. 2013, 743, 87.

    Article  CAS  Google Scholar 

  103. Esmaeilpour, M.; Javidi, J.; Dodeji, F. N.; Abarghoui, M. M. J. Mol. Catal. A: Chem. 2014, 393, 18.

    Article  CAS  Google Scholar 

  104. Esmaeilpour, M.; Javidi, J.; Zahmatkesh, S. Appl. Organomet. Chem. 2016, 30, 897.

    Article  CAS  Google Scholar 

  105. Nanjundaswamy, H. M.; Abrahamse, H. Heterocycles 2014, 89, 2137.

    Article  CAS  Google Scholar 

  106. Habibi, D.; Mostafaee, S.; Mehrabi, L. J. Сhem. Res. 2013, 464.

  107. Darvish, F.; Khazraee, S. Int. J. Org. Chem. 2015, 5, 75.

    Article  CAS  Google Scholar 

  108. Habibi, D.; Nasrollahzadeh, M.; Mehrabi, L.; Mostafaee, S. Monatsh. Chem. 2013, 725.

  109. Wang, H.; Wei, F.; Chen, Q.; Hua, X.; Niu, X. J. Chem. Res. 2016, 40, 570.

    Article  CAS  Google Scholar 

  110. Naeimi, H.; Kiani, F.; Moradian, M. Iran. J. Catal. 2013, 3, 243.

    Google Scholar 

  111. Parveen, M.; Ahmad, F.; Malla, A. M.; Azaz, S. New J. Chem. 2015, 39, 2028.

    Article  CAS  Google Scholar 

  112. Habibi, D.; Nabavi, H.; Nasrollahzadeh, M. J. Chem. 2013, 645313.

  113. Sharghi, H.; Ebrahimpourmoghaddam, S.; Doroodmand, M. M. J. Organomet. Chem. 2013, 738, 41.

    Article  CAS  Google Scholar 

  114. (a) Naeimi, H.; Kiani, F. Ultrason. Sonochem. 2015, 27, 408. (b) Naeimi, H.; Kiani, F.; Moradian, M. J. Nanopart. Res. 2014, 16, 1.

  115. Bahari, S. Lett. Org. Chem. 2013, 10, 527.

    Article  CAS  Google Scholar 

  116. Rostami-Vartooni, A.; Alizadeh, M.; Bagherzadeh, M. Beilstein J. Nanotech. 2015, 6, 2300.

    Article  CAS  Google Scholar 

  117. Karavai, V. P.; Gaponik, P. N.; Ivashkevich, О. А. Magn. Res. Chem. 1989, 27, 611.

    Article  CAS  Google Scholar 

  118. Fallon, F. G.; Herbst, R. M. J. Org. Chem. 1957, 22, 933.

    Article  CAS  Google Scholar 

  119. Shmatova, O. I.; Nenajdenko, V. G. J. Org. Chem. 2013, 78, 18, 9214.

    Article  CAS  Google Scholar 

  120. (a) Zimmerman, D. M.; Olofson, R. A. Tetrahedron Lett. 1969, 5081. (b) Opitz, G.; Merz, W. Justus Liebigs Ann. Chem. 1962, 652, 158.

  121. Grandane, A.; Tanc, M.; Zalubovskis, R.; Supuran, C. T. Bioorg. Med. Chem. 2014, 22, 1522.

    Article  CAS  Google Scholar 

  122. Armour, D. R.; Chung, K. M. L.; Congreve, M.; Evans, B.; Guntrip, S.; Hubbard, T.; Kay, C.; Middlemiss, D.; Mordaunt, J. E.; Pegg, N. A.; Vinader, M. V.; Ward, P.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1015.

    Article  CAS  Google Scholar 

  123. Burukin, A. S.; Vasil'ev, A. A.; Merkulova, N. L.; Struchkova, M. I.; Zlotin, S. G. Russ. Chem. Bull., Int. Ed. 2006, 55, 118. [Izv. Akad. Nauk, Ser. Khim. 2006, 114.]

  124. Tang, Y.; Yang, H.; Shen, J.; Wu, B.; Ju, X.; Lu, C.; Cheng, G. New J. Chem. 2012, 36, 2447.

    Article  CAS  Google Scholar 

  125. Taha, M. A. M.; El-Badry, S. M. J. Korean Chem. Soc. 2010, 54, 414.

    Article  CAS  Google Scholar 

  126. Satoh, Y.; De Lombaert, S.; Marcopulos, N.; Moliterni, J.; Moskal, M.; Tan, J.; Wallace, E. Tetrahedron Lett. 1998, 39, 3367.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Institute for Physical Chemical Problems of the Belarusian State University, 14 Leningradskaya St, 220030, Minsk, Belarus

    Yurii V. Grigoriev & Sergei V. Voitekhovich

  2. Foreign Limited Liability Company BASF, 20 1st Zagorodny Per, 220073, Minsk, Belarus

    Vladimir P. Karavai

  3. Belarusian State University, 4 Nezavisimosti Ave, 220050, Minsk, Belarus

    Oleg A. Ivashkevich

Authors
  1. Yurii V. Grigoriev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sergei V. Voitekhovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vladimir P. Karavai
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Oleg A. Ivashkevich
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Oleg A. Ivashkevich.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 670–681

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Grigoriev, Y.V., Voitekhovich, S.V., Karavai, V.P. et al. Synthesis of tetrazole and its derivatives by heterocyclization reaction involving primary amines, orthoesters, and azides. Chem Heterocycl Comp 53, 670–681 (2017). https://doi.org/10.1007/s10593-017-2108-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2108-7

Keywords

Search

Navigation