The role of potassium ferrocyanide as a catalyst is represented by plausible reaction mechanism.
📌 3 Key Takeaways
🎯
Objective & Hypothesis:In the family of heterocycles that includes benzoxazoles and benzothiazoles, there exist compounds with a wide range of biological activity.
📊
Key Findings & Data:Because of this characteristic, we designed a moderate and effective technique for the synthesis of 2-substituted benzoxazole and benzothiazole using condensation of aldehyde and 2- aminophenol or 2-aminothiophenol via oxidation of carbon-nitrogen bond.
💡
Conclusion & Impact:The role of potassium ferrocyanide as a catalyst is represented by plausible reaction mechanism.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters
Özet
In the family of heterocycles that includes benzoxazoles and benzothiazoles, there exist compounds with a wide range of biological activity. Because of this characteristic, we designed a moderate and effective technique for the synthesis of 2-substituted benzoxazole and benzothiazole using condensation of aldehyde and 2- aminophenol or 2-aminothiophenol via oxidation of carbon-nitrogen bond. Potassium ferrocyanide catalyzed onepot synthesis is efficient and provides for quick reaction times, simple set-up and high yields. As a result, we provide here a technique for the rapid solvent free synthesis of benzoxazoles and benzothiazoles. Some synthesized products were identified by 1H-NMR, 13C-NMR and MASS. The role of potassium ferrocyanide as a catalyst is represented by plausible reaction mechanism.
🔖
Cite This Article
PATIL, V. S., PATIL, D. V., POTDAR, S. S. (2022). Potassium ferrocyanide promoted an efficient synthesis of benzoxazoles and benzothiazoles under solvent free condition. Organic Communications, Cilt: 15 - Sayı: 1, 71–80. https://ajindex.com/articles/417561
Chaney, M. O.; Demarco, P. V.; Jones, N. D.; Occolowitz, J. L. Structure of A23187, a divalent cation ionophore. J. Am. Chem. Soc. 1974, 96, 1932-1933
Sato, S.; Kajiura, T.; Noguchi, M.; Takehana, K.; Kobayasho, T.; Tsuji, T. AJI9561, a new cytotoxic benzoxazole derivative produced by streptomyces sp. J. Antibiot. 2001, 54, 102-104
Brown, R. N.; Cameron, R.; Chalmers, D. K.; Hamilton, S.; Luttick, A.; Krippner, G. Y.; McConnell, D. B.; Nearn, R.; Stanislawski, P. C.; Tucker, S. P.; Watson, K. G. 2-Ethoxybenzoxazole as a bioisosteric replacement of an ethyl benzoate group in a human rhinovirus (HRV) capsid binder. Bioorg. Med. Chem. Lett. 2005, 15, 2051-2055 [4] Manas, E. S.; Unwalla, R. J.; Xu, Z. B.; Malamas, M. S.; Miller, C. P.; Harris, H. A.; Hsiao, C.; Akopian, T.; Hum, W. T.; Malakian, K.; Wolfrom, S.; Bapat, A.; Bhat, R. A.; Stahl, M. L.; Somers, W. S.; Alvarez, J. C. Structure-based design of estrogen receptor-β selective ligands. J. Am. Chem. Soc. 2004, 126, 15106-15119
Malamas, M. S.; Manas, E. S.; McDevitt, R. E.; Gunawan, I.; Xu, Z. B.; Collini, M. D.; Miller, C. P.; Dinh, T.; Henderson, R. A.; Keith, J. C.; Harris, H. A. Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-β ligands. J. Med. Chem. 2004, 47, 5021
Prudhomme, M.; Guyot, J.; Jeminet, G. Semi-synthesis of a23187 (calcimycin) analogs. J. Antibiot. 1986, 39, 934–937
Ren, I. O.; Temiz, O.; Yalcin, I.; Sener, E. Akin, A.; Ucarturk N. Synthesis and microbiological activity of 5(or 6)-methyl-2-substituted benzoxazole and benzimidazole derivatives. Arzneim Forsch. Drug Res. 1997, 47, 1393–1397
Ren, I. O.; Temiz, O.; Yalcın I.; Aki-Sener, E.; Altanlar, N. Synthesis and antimicrobial activity of some novel 2,5- and/or 6-substituted benzoxazole and benzimidazole derivatives. Eur. J. Pharm. Sci. 1999, 7, 153– 160
Temiz-Arpaci, O.; Ozdemir, A.; Yalcin, I.; Yildiz, I.; Aki-Sener, E.; Altanlar, N. Synthesis and antimicrobial activity of some 5-[2-(Morpholin-4-yl)acetamido] and/or 5-[2-(4-Substituted piperazin-1-yl)acetamido]-2-(psubstituted phenyl)benzoxazoles. Arch. Pharm. 2005, 338, 105–111
Vinsova, J.; Horak, V.; Buchta, V.; Kaustova, J. Highly lipophilic benzoxazoles with potential antibacterial activity. Molecules 2005, 10, 783–793
Song, X.; Vig, B. S.; Lorenzi, P. L.; Drach, J. C.; Townsend, L. B.; Amidon, G. L. Amino acid ester prodrugs of the antiviral agent 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)be