Research Article


DOI :10.26650/IstanbulJPharm.2019.19002   IUP :10.26650/IstanbulJPharm.2019.19002    Full Text (PDF)

A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines

Çağla Begüm ApaydınZafer Cesur

This report is about an unexpected formation of N,N’-bis(substituted phenoxyacetyl) hydrazine derivatives. The reaction between N’-(4-ethylcyclohexylidene)phenoxyacetohydrazide with sulfanyl acids to obtain 4-thiazolidinones s, gave an unexpected product, N,N’-bis(phenoxyacetyl)hydrazine, with high purity instead of the expected cyclocondensation product. When repeating the reaction with p-toluenesulfonic acid under the same conditions, the reaction resulted in the same compound. This indicates that two molecules of N’-(4-ethylcyclohexylidene)phenoxyacetohydrazide were involved in the reaction. The reaction can be applied as a different and new procedure for the synthesis of several N,N’-bis(substituted phenoxyacetyl) hydrazine derivatives.


PDF View

References

  • Baltazzi E, Delavigne R (1955). Hydrazides of the Phenoxyacetic acid series and derivatives. Compt Rend 241: 633-635. google scholar
  • Hamama WS, Mohamed AI, Shaaban S, Zoorob HH. (2008). Progress in the Chemistry of 4- Thiazolidinones. J Heterocycl Chem 45: 939-956. google scholar
  • Kocabalkanlı A, Cihan-Üstündağ G, Naesens L, Mataracı-Kara E, Nassozi M, Çapan G. (2017). Diclofenac-Based Hydrazones and Spirothiazolidinones: Synthesis, Characterization, and Antimicrobial Properties. Arch Pharm Chem Life Sci 350: e1700010. google scholar
  • Mirek J (1958). Urethans as regulators of plant growth. Zesz Nauk Uniw 4: 163-170. google scholar
  • Patai S (1970). The chemistry of amides. In: Zabicky J (ed) The chemistry of hydrazides, John Wiley & Sons, New York, pp. 533-535. google scholar
  • Singh SP, Parmar SS, Raman K, Stenberg VI (1981). Chemistry and Biological Activity of Thiazolidinones. Chem Rev 81: 175-203. google scholar
  • Sun J, Zhou Y (2015). Design, Synthesis, and Insecticidal Activity of Some Novel Diacylhydrazine and Acylhydrazone Derivatives. Molecules 20: 5625-5637. google scholar
  • Tripathi AC, Gupta SJ, Fatima GN, Sonar PK, Verma A, Saraf SK (2014). 4-Thiazolidinones: The advances continue. Eur J Med Chem 72: 52-77. google scholar
  • Wang H, Yang Z, Fan Z, Wu Q, Zhang Y, Mi N, Wang S, Zhang Z, Song H, Liu F (2011). Synthesis and Insecticidal Activity of N-tert-Butyl-N,N’-diacylhydrazines Containing 1,2,3-Thiadiazoles. J Agric Food Chem 59: 628-634. google scholar
  • Zawadowsca I (1961). The reaction of ethyl acetoacetate with some hydrazides of phenoxyacetic acids. Acta Pol Pharm 18: 401-407. google scholar

Citations

Copy and paste a formatted citation or use one of the options to export in your chosen format


EXPORT



APA

Apaydın, Ç., & Cesur, Z. (0001). A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines. İstanbul Journal of Pharmacy, 49(2), 61-63. https://doi.org/10.26650/IstanbulJPharm.2019.19002


AMA

Apaydın Ç, Cesur Z. A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines. İstanbul Journal of Pharmacy. 0001;49(2):61-63. https://doi.org/10.26650/IstanbulJPharm.2019.19002


ABNT

Apaydın, Ç.; Cesur, Z. A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines. İstanbul Journal of Pharmacy, [Publisher Location], v. 49, n. 2, p. 61-63, 0001.


Chicago: Author-Date Style

Apaydın, Çağla Begüm, and Zafer Cesur. 0001. “A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines.” İstanbul Journal of Pharmacy 49, no. 2: 61-63. https://doi.org/10.26650/IstanbulJPharm.2019.19002


Chicago: Humanities Style

Apaydın, Çağla Begüm, and Zafer Cesur. A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines.” İstanbul Journal of Pharmacy 49, no. 2 (Sep. 2024): 61-63. https://doi.org/10.26650/IstanbulJPharm.2019.19002


Harvard: Australian Style

Apaydın, Ç & Cesur, Z 0001, 'A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines', İstanbul Journal of Pharmacy, vol. 49, no. 2, pp. 61-63, viewed 27 Sep. 2024, https://doi.org/10.26650/IstanbulJPharm.2019.19002


Harvard: Author-Date Style

Apaydın, Ç. and Cesur, Z. (0001) ‘A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines’, İstanbul Journal of Pharmacy, 49(2), pp. 61-63. https://doi.org/10.26650/IstanbulJPharm.2019.19002 (27 Sep. 2024).


MLA

Apaydın, Çağla Begüm, and Zafer Cesur. A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines.” İstanbul Journal of Pharmacy, vol. 49, no. 2, 0001, pp. 61-63. [Database Container], https://doi.org/10.26650/IstanbulJPharm.2019.19002


Vancouver

Apaydın Ç, Cesur Z. A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines. İstanbul Journal of Pharmacy [Internet]. 27 Sep. 2024 [cited 27 Sep. 2024];49(2):61-63. Available from: https://doi.org/10.26650/IstanbulJPharm.2019.19002 doi: 10.26650/IstanbulJPharm.2019.19002


ISNAD

Apaydın, Çağla Begüm - Cesur, Zafer. A new approach for the synthesis of N,N’- bis(phenoxyacetyl)hydrazines”. İstanbul Journal of Pharmacy 49/2 (Sep. 2024): 61-63. https://doi.org/10.26650/IstanbulJPharm.2019.19002



TIMELINE


Accepted02.04.2019

LICENCE


Attribution-NonCommercial (CC BY-NC)

This license lets others remix, tweak, and build upon your work non-commercially, and although their new works must also acknowledge you and be non-commercial, they don’t have to license their derivative works on the same terms.


SHARE




Istanbul University Press aims to contribute to the dissemination of ever growing scientific knowledge through publication of high quality scientific journals and books in accordance with the international publishing standards and ethics. Istanbul University Press follows an open access, non-commercial, scholarly publishing.