Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Synthesis and reactivity of a triphenyltin-functionalized 1H-(3,5-dimethylpyrazol-1-ylmethyl)-1,2,3-benzotriazole

Abstract

Treatment of 1H-(3,5-dimethylpyrazol-1-ylmethyl)-1,2,3-benzotriazole [CH2(3,5-Me2Pz)(Bt)] with one equivalent of n-BuLi followed by Ph3SnCl gave a ditin derivative [(Ph3Sn)2C(3,5-Me2Pz)(Bt)]. Use of two equivalents of n-BuLi gave CH2(3,5-Me2Pz)(Bt-SnPh3) together with (Ph3Sn)2C(3,5-Me2Pz)(Bt). Reaction of (Ph3Sn)2C(3,5-Me2Pz)(Bt) with W(CO)5(THF) gave (Ph3Sn)2C(3,5-Me2Pz)(BtW(CO)5), while the reaction of CH2(3,5-Me2Pz)(Bt-SnPh3) with W(CO)5(THF) resulted in the formation of three complexes, namely CH2(3,5-Me2Pz)(Bt-SnPh3)W(CO)5, CH2(3,5-Me2Pz)(Bt-SnPh3)W(CO)4 and CH2(3,5-Me2Pz)(Bt)W(CO)4. All of these products have been characterized by physicochemical and spectroscopic methods. In addition, the structures of five of the compounds have been confirmed by X-ray structural analyses, revealing that the functionalized 1H-(3,5-dimethylpyrazol-1-ylmethyl)-1,2,3-benzotriazole has variable coordination modes.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

References

  1. 1.

    Pettinari C, Pettinari R (2005) Coord Chem Rev 249:663

  2. 2.

    Otero A, Fernández-Baeza J, Lara-Sánchez A, Tejeda J, Sánchez-Barba LF (2008) Eur J Inorg Chem 5309

  3. 3.

    Otero A, Fernández-Baeza J, Lara-Sánchez A, Sánchez-Barba LF (2013) Coord Chem Rev 257:1806

  4. 4.

    Watson AA, House DA, Steel PJ (1995) Aust J Chem 48:1549

  5. 5.

    Otero A, Fernández-Baeza J, Antiñolo A, Tejeda J, Lara-Sánchez A, Sánchez-Barba L, Expósito MT, Rodríguez AM (2003) Dalton Trans 1614

  6. 6.

    Hegelmann I, Beck A, Eichhorn C, Weibert B, Burzlaff N (2003) Eur J Inorg Chem 339

  7. 7.

    Santini C (2004) Inorg Chem Commun 7:834

  8. 8.

    An CX, Han XL, Wang PB, Zhang ZH, Zhang HK, Fan ZJ (2008) Transition Met Chem 33:835

  9. 9.

    Li F, Hor TSA (2008) Adv Synth Catal 350:2391

  10. 10.

    Meng X, Jin S, Hou H, Du C, Ng SW (2009) Inorg Chim Acta 362:1519

  11. 11.

    Meng X, Zhu X, Qi Y, Hou H, Fan Y (2009) J Mol Struct 934:28

  12. 12.

    Duan L, Ding Y, Meng X, Li W, Hou H, Fan Y (2010) J Mol Struct 975:53

  13. 13.

    Zhou X, Li W, Jin G, Zhao D, Zhu X, Meng X, Hou H (2011) J Mol Struct 995:148

  14. 14.

    Li HJ, Liu XL, Ding K, Song HB, Tang LF (2014) J Organomet Chem 757:8

  15. 15.

    Ding K, Sun ZM, Li HQ, Tang LF (2015) Chin J Inorg Chem 31:345

  16. 16.

    Yang H, Liu PY, Song HB, Tang LF (2015) Chin J Struct Chem 34:1742

  17. 17.

    Potapov AS, Nudnova EA, Khlebnikov AI, Ogorodnikov VD (2010) Izvestiya Vysshikh Uchebnykh Zavedenii. Khimiyai Khimicheskaya Tekhnol 53:30

  18. 18.

    Katritzky AR, Drewniak-Dyrup M, Lan X, Brunner F (1989) J Heterocyclic Chem 26:829

  19. 19.

    Katritzky AR, Maimait R, Xu YJ, Gyoung YS (2002) J Org Chem 67:8230

  20. 20.

    Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) J Appl Cryst 42:339

  21. 21.

    CrystalStructure 3.7.0, Crystalclear 1.36 (2000) Crystal structure analysis package. Rigaku and Rigaku/MSC, TX

  22. 22.

    Palatinus L, Prathapa SJ, van Smaalen S (2012) J Appl Cryst 45:575

  23. 23.

    Sheldrick GM (2008) Acta Crystallogr A 64:112

  24. 24.

    Spek AL (2003) J Appl Cryst 36:7

  25. 25.

    Bondi A (1964) J Phys Chem 68:441

  26. 26.

    Tang LF, Zhao SB, Jia WL, Yang Z, Song DT, Wang JT (2003) Organometallics 22:3290

  27. 27.

    Buffin BP, Poss MJ, Arif AM, Richmond TG (1993) Inorg Chem 32:3805

  28. 28.

    Kraihanzel CS, Cotton FA (1963) Inorg Chem 2:533

  29. 29.

    Orgel LE (1962) Inorg Chem 1:25

  30. 30.

    Cheng CH, Guo RY, Cui Q, Song HB, Tang LF (2015) Transition Met Chem 40:297

Download references

Acknowledgments

This work is supported by the National Natural Science Foundation of China (No. 21372124).

Author information

Correspondence to Liang-Fu Tang.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Yang, H., Li, S. & Tang, L. Synthesis and reactivity of a triphenyltin-functionalized 1H-(3,5-dimethylpyrazol-1-ylmethyl)-1,2,3-benzotriazole. Transit Met Chem 41, 655–661 (2016). https://doi.org/10.1007/s11243-016-0065-0

Download citation

Keywords

  • Pyrazole
  • Triazolyl
  • Benzotriazole
  • Pyrazolyl
  • Tetrahedral Geometry