Journals / Turkish Journal of Chemistry / 2019 / Cilt: 43 - Sayı: 4

N -Acylazole mediated stereoselective and regioselective synthesis of N -substituted azole acrylonitriles

Pages
1134–1148
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 structural determinations were accomplished by NOESY 1 H NMR and X-ray crystallography.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Regio- and stereoselective synthesis of N -substituted azole acrylonitriles has been achieved smoothly inN, N -dimethylformamide (DMF) in the presence of potassium carbonate (K2 CO3) as a base catalyst.
📊
Key Findings & Data:N -Substituted azole acrylonitriles were obtained in moderate to good yields (39%–87%) with a one-pot reaction between readily available N -acetylazoles and Baylis-Hillman nitriles.
💡
Conclusion & Impact:The structural determinations were accomplished by NOESY 1 H NMR and X-ray crystallography.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

Regio- and stereoselective synthesis of N -substituted azole acrylonitriles has been achieved smoothly inN, N -dimethylformamide (DMF) in the presence of potassium carbonate (K2 CO3) as a base catalyst. N -Substituted azole acrylonitriles were obtained in moderate to good yields (39%–87%) with a one-pot reaction between readily available N -acetylazoles and Baylis-Hillman nitriles. The structural determinations were accomplished by NOESY 1 H NMR and X-ray crystallography.

🔖

Cite This Article

AYDIN, O., KÖKTEN, Ş., ÇELİK, İ., ÜNVER, H. (2022). N -Acylazole mediated stereoselective and regioselective synthesis of N -substituted azole acrylonitriles. Turkish Journal of Chemistry, Cilt: 43 - Sayı: 4, 1134–1148. https://ajindex.com/articles/601732

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (12)

  1. Al-Omran F, Mohareb RM, El-Khair AA. Synthesis and biological effects of new derivatives of benzotriazole as antimicrobial and antifungal agents. Journal of Heterocyclic Chemistry 2002
  2. doi: 10.1002/jhet.5570390504 2. Moon WS, Chung KH, Seol DJ, Park ES, Shim JH et al. Antimicrobial effect of monomers and polymers with azole moieties. Journal of Applied Polymer Science 2003
  3. doi: 10.1002/app.13019 3. Al-Soud YA, Al-Masoudib NA, Ferwanah AES. Synthesis and properties of new substituted 1,2,4-triazoles: Potential antitumor agents. Bioorganic and Medicinal Chemistry 2003
  4. doi: 10.1016/S0968-0896(03)00043- 9 4. Pawar SS, Gorde PL, Kakde RB. Synthesis of new N1 -substituted benzotriazoles as anthelmintic agents. Archives of Applied Science Research 2010
  5. 2 (1): 80-85. 5. Kopanska K, Najda A, Zebrowska J, Chomicz L, Piekarczyk J et al. Synthesis and activity of 1H -benzimidazole and 1H -benzotriazole derivatives as inhibitors of Acanthamoeba castellanii. Bioorganic and Medicinal Chemistry 2004
  6. doi: 10.1016/j.bmc.2004.03.022 6. Suma BV, Natesh NN, Madhavan V. Benzotriazole in medicinal chemistry: An overview. Journal of Chemical and Pharmaceutical Research 2011
  7. 3 (6): 375-381. 7. Walia R, Hedaitullah M, Naaz S F, Iqbal K, Lamba H. Benzimidazole derivatives – an overview. International Journal of Research in Pharmacy and Chemistry. 2011
  8. 1 (3): 565-574. 8. Velik J, Baliharova V, Fink-Gremmels J, Bull S, Lamka J et al. Benzimidazole drugs and modulation of biotransformation enzymes. Research in Veterinary Science 2004
  9. doi: 10.1016/j.rvsc.2003.08.005 9. Carlini P, Bria E, Giannarelli D, Ferretti G, Felici A et al. New aromatase inhibitors as second-line endocrine therapy in postmenopausal patients with metastatic breast carcinoma. Cancer 2005
  10. 104 (7): 1335-1342. doi: 10.1002/cncr.21339 10. Joss RA, Galeazzi RL, Bischoff AK, Brunner KW. Alizapride, a new substituted benzamide, as an antiemetic during cancer chemotherapy. European Journal of Clinical Pharmacology 1985
  11. doi: 10.1007/BF00547056 11. Asteinza J Camacho-Carranza R, Reyes-Reyes R E, Dorado-González V Espinosa-Aguirre JJ. Induction of cytochrome P450 enzymes by albendazole treatment in the rat. Environmental Toxicology and Pharmacology 2000
  12. doi: 10.1016/S1382-6689(00)00059-4 12. Radice S, Marabini L, Gervasoni M, Ferraris M, Chiesara E. Carbendazim and n-butylisocyanate: metabolites responsible for benomyl do