SavedAdd your journal

Journals / Turkish Journal of Chemistry / 2017 / Cilt: 41 - Sayı: 3

Stereoselective and regioselective synthesis of NN-substituted methyl 2-((azolyl)methyl)-3-arylacrylates from Baylis-Hillman acetates

İlhami ÇELİK
Ayşen KÖSECELİ ÖZENÇ
Şule KÖKTEN
Pages
323–334
Publication Date
2022-11-05
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The targeted N -substituted azole acrylates were efficiently obtained in good yields (39% 89%).

📌 3 Key Takeaways

🎯
Objective & Hypothesis:N -Substituted methyl 2-((azolyl)methyl)-3-arylacrylates were synthesized stereo- and regioselectively with one-pot reaction between Baylis Hillman acetates and a suitable acylazole in the presence of K2 CO3 as a base catalyst.
📊
Key Findings & Data:N -Substituted methyl 2-((azolyl)methyl)-3-arylacrylates were synthesized stereo- and regioselectively with one-pot reaction between Baylis Hillman acetates and a suitable acylazole in the presence of K2 CO3 as a base catalyst.
💡
Conclusion & Impact:The targeted N -substituted azole acrylates were efficiently obtained in good yields (39% 89%).
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

N -Substituted methyl 2-((azolyl)methyl)-3-arylacrylates were synthesized stereo- and regioselectively with one-pot reaction between Baylis Hillman acetates and a suitable acylazole in the presence of K2 CO3 as a base catalyst. The targeted N -substituted azole acrylates were efficiently obtained in good yields (39% 89%).

🔖

Cite This Article

ÇELİK, İ., ÖZENÇ, A. K., KÖKTEN, Ş. (2022). Stereoselective and regioselective synthesis of NN-substituted methyl 2-((azolyl)methyl)-3-arylacrylates from Baylis-Hillman acetates. Turkish Journal of Chemistry, Cilt: 41 - Sayı: 3, 323–334. https://ajindex.com/articles/601936

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (28)

  1. Kathiravan, M. K.; Salake, A. B.; Chothe, A. S.; Dudhe, P. B.; Watode, R. P.; Mukta, M. S.; Gadhwe, S. Bioorg. Med. Chem. 2012, 20, 5678-5698
  2. El-Garhy, O. H. Int. J. Curr. Pharm. Res. 2015, 7, 1-6
  3. Heeres, J.; Backx, L. J.; Mostmans, J. H.; Van Cutsem, J. J. Med. Chem. 1979, 22, 1003-1005
  4. McTavish, D.; Buckly, M. M. T.; Heel, R. C. Drugs 1991, 42, 138-170
  5. Bleiberg, H.; Gerard, B.; Dalesio, O.; Crespeigne, N.; Rozeneweig, M. Cancer Chemother. Pharmacol. 1998, 22, 316-320
  6. Bellina, F.; Guazzelli, N.; Lessi, M.; Manzini, C. Tetrahedron 2015, 71, 2298-2305
  7. Takahashi, K.; Hashimoto, N.; Nakama, C.; Kamata, K.; Sasaki, K.; Yoshimoto, R.; Ohyama, S.; Hosaka, H.; Maruki, H.; Nagata, Y. et al. Bioorg. Med. Chem. 2009, 17, 7042-7051
  8. Loddo, R.; Novelli, F.; Sparatore, A.; Tasso, B.; Tonelli, M.; Boido, V.; Sparatore, F.; Collu, G.; Delogu, I.; Giliberti, G. et al. Bioorg. Med. Chem. 2015, 23, 7024-7034
  9. Kuznetsov, Y. I.; Kazansky, L. P. Russian Chem. Rev. 2008, 77, 219-232
  10. Liu, Z.; Tan, L.; Wu, Q.; Lin, X. Chin. J. Chem. 2012, 30, 2343-2348
  11. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891
  12. Lee, H. S.; Kim, S. H.; Gowrisankar, S.; Kim, J. N. Tetrahedron 2008, 64, 7183-7190
  13. Rodrigues M. T. Jr; Santos, M. S.; Santos, H.; Coelho, F. Tetrahedron Lett. 2014, 55, 180-183
  14. Ye, D.; Li, J.; Li, C.; Jia, X. Chinese J. Chem. 2009, 27, 1159-1162
  15. Li, J.; Liu, Y. K.; Zhang, Y. M. Chinese Chem. Lett. 2006, 17, 877-879
  16. Li, J.; Wang, X.; Zhang, Y. Tetrahedron Lett. 2005, 46, 5233-5237
  17. Paul, R.; Anderson, G. W. J. Am. Chem. Soc. 1960, 82, 4596-4600
  18. Kamijo, T.; Yamamoto, R.; Harada, H.; Iizuka, K. Chem. Pharm. Bull. 1982, 30, 4242-4244
  19. Kanı¸skan, N.; K¨okten, S¸.; C¸ elik, ˙I. Arkivoc 2012, 2012, 198-213
  20. Kim, B. R.; Sung, G. H.; Lee, S. G.; Yoon, Y. J. Tetrahedron 2013, 69, 3234-3237
  21. K¨okten, S¸.; C¸ elik, ˙I. Synthesis 2013, 45, 2551-2556
  22. Leiris, S. J.; Khdour, O. M.; Segerman, Z. J.; Tsosie, K. S.; Chapuis, J. C.; Hecht, S. M. Bioorg. Med. Chem. 2010, 18, 3481-3493
  23. Lim, D.; Fang, F.; Zhou, G.; Coltart, D. M. Org. Lett. 2007, 9, 4139-4142
  24. K¨okten, S¸.; C¸ elik, ˙I. Tetrahedron Lett. 2015, 56, 6254-6256
  25. Chaturvedi, A. K.; Rastogi, N. Synthesis 2015, 47, 249-255
  26. Hoffmann, H. M. R.; Rabe, J. Angew. Chem. Int. Ed. Engl. 1983, 22, 795-796
  27. O’Del, D. K.; Nicholas, K. M. J. Org. Chem. 2003, 68, 6427-6430
  28. Shadakshari, U.; Nayak, S. K. Tetrahedron