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

Abstract

DOI: 10.26650/IstanbulJPharm.2019.19002

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. 

Cite this article as: Apaydın ÇB, Cesur Z (2019). A new approach for the synthesis of N,N’-bis(phenoxyacetyl)hydrazines. Istanbul J Pharm 49 (2): 61-63.

Keywords

• Diacylhydrazines,sulfanyl acid,reaction mechanism

References

1. Baltazzi E, Delavigne R (1955). Hydrazides of the Phenoxyacetic acid series and derivatives. Compt Rend 241: 633-635. Hamama WS, Mohamed AI, Shaaban S, Zoorob HH. (2008). Progress in the Chemistry of 4- Thiazolidinones. J Heterocycl Chem 45: 939-956. 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. Mirek J (1958). Urethans as regulators of plant growth. Zesz Nauk Uniw 4: 163-170. Patai S (1970). The chemistry of amides. In: Zabicky J (ed) The chemistry of hydrazides, John Wiley & Sons, New York, pp. 533-535. Singh SP, Parmar SS, Raman K, Stenberg VI (1981). Chemistry and Biological Activity of Thiazolidinones. Chem Rev 81: 175-203. Sun J, Zhou Y (2015). Design, Synthesis, and Insecticidal Activity of Some Novel Diacylhydrazine and Acylhydrazone Derivatives. Molecules 20: 5625-5637. 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. 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. Zawadowsca I (1961). The reaction of ethyl acetoacetate with some hydrazides of phenoxyacetic acids. Acta Pol Pharm 18: 401-407.