Skip to main content

Benzothiazolyl- and benzimidazolyl-substituted 1-iminoisoindolines: synthesis, mechanistic studies, and crystal structure determination

Abstract

New benzothiazolyl- and benzimidazolyl-substituted 1-iminoisoindolines are prepared in the reaction of o-phthalaldehyde and substituted 2-aminobenzothiazoles and 2-aminobenzimidazoles. The optimization of these reactions is discussed, and the reaction mechanisms are proposed based on the experimental findings. Isoindolines with other heterocyclic substituents are prepared as a confirmation of the proposed mechanisms. Molecular and crystal structures of several prepared compounds are determined by a single crystal X-ray diffraction. These structures are found to be in line with projections based on the chemical and spectroscopic properties, and thus offer an additional confirmation of the proposed reaction mechanisms.

Graphical abstract

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

References

  1. 1.

    Rothweiler W, Tamm C (1966) Experientia 22:750

    CAS  Article  Google Scholar 

  2. 2.

    Aldridge DC, Armstrong JJ, Speake RN, Turner, WB (1967) Chem Commun:26

  3. 3.

    Kundu N, Khan MW, Mukhopadhyay R (2001) J Indian Chem Soc 78:671

    CAS  Google Scholar 

  4. 4.

    Abdel-Aziz AA, El Tahir KE, Asiri YA (2011) Eur J Med Chem 46:1648

    CAS  Article  Google Scholar 

  5. 5.

    Belliotti TR, Brink WA, Kesten SR, Rubin JR (1998) Bioorg Med Chem Lett 8:1499

    CAS  Article  Google Scholar 

  6. 6.

    Norman MH, Minick DJ, Rigdon GC (1996) J Med Chem 39:149

    CAS  Article  Google Scholar 

  7. 7.

    Luci DK, Lawson EC, Ghosh S, Kinney WA, Smith CE, Qi J, Wang Y, Minor LK, Maryanoff BE (2009) Tetrahedron Lett 50:4958

    CAS  Article  Google Scholar 

  8. 8.

    Lawson EC, Luci DK, Ghosh S, Kinney WA, Reynolds CH, Qi J, Smith CE, Wang Y, Minor LK, Haertlein BJ, Parry TJ, Damiano BP, Maryanoff BE (2009) J Med Chem 52:7432

    CAS  Article  Google Scholar 

  9. 9.

    Berger D, Citarella R, Dutia M, Greenberger L, Hallett W, Paul R, Powell D (1999) J Med Chem 42:2145

    CAS  Article  Google Scholar 

  10. 10.

    Masterson LA, Croker SJ, Jenkins TC, Howard PW, Thurston DE (2004) Bioorg Med Chem Lett 14:901

    CAS  Article  Google Scholar 

  11. 11.

    Curtin ML, Frey RR, Heyman HR, Sarris KA, Steinman DH, Holmes JH, Bousquet PF, Cunha GA, Moskey MD, Ahmed AA, Pease LJ, Glaser KB, Stewart KD, Davidsen SK, Michaelides MR (2004) Bioorg Med Chem Lett 14:4505

    CAS  Article  Google Scholar 

  12. 12.

    Jiaang W-T, Chen J-S, Hsu T, Wu S-H, Chien C-H, Chang C-N, Chang S-P, Lee S-J, Chen X (2005) Bioorg Med Chem Lett 15:687

    CAS  Article  Google Scholar 

  13. 13.

    Van Goethem S, Van der Veken P, Dubois V, Soroka A, Lambeir A-M, Chen X, Haemers A, Scharpe S, De Meester I, Augustyns K (2008) Bioorg Med Chem Lett 18:4159

    Article  Google Scholar 

  14. 14.

    Meggers E, Atilla-Gokcumen GE, Bregman H, Maksimoska J, Mulcahy SP, Pagano N, Williams DS (2007) Synlett 8:1177

    Article  Google Scholar 

  15. 15.

    Kaizer J, Kripli B, Speier G, Parkanyi L (2009) Polyhedron 28:933

    CAS  Article  Google Scholar 

  16. 16.

    Chitanda JM, Prokopchuk DE, Quail JW, Foley SR (2008) Organometallics 27:2337

    CAS  Article  Google Scholar 

  17. 17.

    Broering M, Kleeberg C, Koehler S (2008) Inorg Chem 47:6404

    CAS  Article  Google Scholar 

  18. 18.

    Broering M, Kleeberg C (2009) Inogr Chim Acta 362:1065

    CAS  Article  Google Scholar 

  19. 19.

    Takahashi I, Hatanaka M (1997) Heterocycles 45:2475

    CAS  Article  Google Scholar 

  20. 20.

    Wan J, Wu B, Pan Y (2007) Tetrahedron 63:9338

    CAS  Article  Google Scholar 

  21. 21.

    Wan J-P, Zhou J, Mao H, Pan Y-J, Wu A-X (2008) Tetrahedron 64:11115

    CAS  Article  Google Scholar 

  22. 22.

    Cul A, Daich A, Decroix B, Sanz G, Van Hijfte L (2004) Tetrahedron 60:11029

    CAS  Article  Google Scholar 

  23. 23.

    Souvie J-C, Fugire C, Lecouve J-P (2001) Process for the preparation of isoindoline. U.S. Patent 6320058 B2. Chem Abstr 135:195499

  24. 24.

    Yoshida H, Fukushima H, Ohshita J, Kunai A (2004) Tetrahedron Lett 45:8659

    CAS  Article  Google Scholar 

  25. 25.

    Shen S, Xu X, Lei M, Hu L (2012) Synthesis 44:3543

    CAS  Article  Google Scholar 

  26. 26.

    Hu L-J, Zhan Z-J, Lei M, Hu L-H (2013) Arkivoc 2013:189

    Article  Google Scholar 

  27. 27.

    You H, Chen F, Lei M, Hu L (2013) Tetrahedron Lett 54:2972

    CAS  Article  Google Scholar 

  28. 28.

    Chen F, Lei M, Hu L (2014) Green Chem 16:2472

    CAS  Article  Google Scholar 

  29. 29.

    Sole D, Serrano O (2010) J Org Chem 75:6267

    CAS  Article  Google Scholar 

  30. 30.

    Zang Q, Javed S, Porubsky P, Ullah F, Neuenswander B, Lushington GH, Basha FZ, Organ MG, Hanson PR (2012) ACS Comb Sci 14:211

    CAS  Article  Google Scholar 

  31. 31.

    Priebbenow DL, Stewart SG, Pfeffer FM (2011) Org Biomol Chem 9:1508

    CAS  Article  Google Scholar 

  32. 32.

    Chen K, Pullarkat SA (2012) Org Biomol Chem 10:6600

    CAS  Article  Google Scholar 

  33. 33.

    Fustero S, Moscardo J, Sanchez-Rosello M, Rodriguez E, Barrio P (2010) Org Lett 12:5494

    CAS  Article  Google Scholar 

  34. 34.

    Fustero S, Herrera L, Lazaro R, Rodriguez E, Maestro MA, Mateu N, Barrio P (2013) Chem Eur J 19:11776

    CAS  Article  Google Scholar 

  35. 35.

    Tamgho I-S, Engle JT, Ziegler CJ (2013) Tetrahedron Lett 54:6114

    CAS  Article  Google Scholar 

  36. 36.

    He ZL, Liu TL, Tao HY, Wang CJ (2012) Org Lett 14:6230

    CAS  Article  Google Scholar 

  37. 37.

    Takahashi I, Miyamoto R, Nishiuchi K, Hatanaka M, Yamano A, Sakushima A, Hosoi S (2004) Heterocycles 63:1267

    CAS  Article  Google Scholar 

  38. 38.

    Takahashi I, Nishiuchi K, Miyamoto R, Hatanak M, Uchida H, Isa K, Sakushima A, Hosoi S (2005) Lett Org Chem 2:40

    CAS  Article  Google Scholar 

  39. 39.

    Sović I, Stilinović V, Kaitner B, Kraljević Pavelić S, Bujak M, Čuljak K, Novak P, Karminski-Zamola G (2011) J Mol Struct 1006:259

  40. 40.

    Sović I, Kraljević Pavelić S, Markova-Car E, Ilić N, Nhili R, Depauw S, David-Cordonnier M-H, Karminski-Zamola G (2014) Eur J Med Chem 87:372

  41. 41.

    Ćaleta I, Grdiša M, Mrvoš-Sermek D, Cetina M, Tralić-Kulenović V, Pavelić K, Karminski-Zamola G (2004) Il Farmaco 59:297

    Article  Google Scholar 

  42. 42.

    Starčević K, Ćaleta I, Cinčić D, Kaitner B, Kralj M, Ester K, Karminski-Zamola G (2006) Heterocycles 68:2285

    Article  Google Scholar 

  43. 43.

    Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG (1987) J Chem Soc Perkin Trans 2:S1

    Article  Google Scholar 

  44. 44.

    Blagus A, Cinčić D, Friščić T, Kaitner B, Stilinović V (2010) Maced J Chem Chem Eng 29:117

    CAS  Google Scholar 

  45. 45.

    Stilinović V, Cinčić D, Zbačnik M, Kaitner B (2012) Croat Chem Acta 85:485

    Article  Google Scholar 

  46. 46.

    Oxford Diffraction (2003) CrysAlis CCD and CrysAlis RED, version 1.170. Oxford Diffraction Ltd, Wroclaw

  47. 47.

    Sheldrick GM (2008) Acta Cryst A64:112

    Article  Google Scholar 

  48. 48.

    Farrugia LJ (1999) J Appl Cryst 32:837

    CAS  Article  Google Scholar 

Download references

Acknowledgments

This work was financially supported by Croatian Science Foundation (project No. 5596).

Author information

Affiliations

Authors

Corresponding authors

Correspondence to Irena Sović or Grace Karminski-Zamola.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Sović, I., Orehovec, I., Stilinović, V. et al. Benzothiazolyl- and benzimidazolyl-substituted 1-iminoisoindolines: synthesis, mechanistic studies, and crystal structure determination. Monatsh Chem 147, 1825–1837 (2016). https://doi.org/10.1007/s00706-016-1796-5

Download citation

Keywords

  • Heterocycles
  • Reaction mechanisms
  • Schiff bases
  • X-ray structure determination