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

Year 2019, Volume: 49 Issue: 2, 61 - 63, 01.08.2019

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.

References

  • 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.
Year 2019, Volume: 49 Issue: 2, 61 - 63, 01.08.2019

Abstract

References

  • 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.
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Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Original Article
Authors

Çağla Begüm Apaydın

Zafer Cesur This is me

Publication Date August 1, 2019
Submission Date February 11, 2019
Published in Issue Year 2019 Volume: 49 Issue: 2

Cite

APA Apaydın, Ç. B., & Cesur, Z. (2019). A new approach for the synthesis of N,N’-bis(phenoxyacetyl)hydrazines. İstanbul Journal of Pharmacy, 49(2), 61-63.
AMA Apaydın ÇB, Cesur Z. A new approach for the synthesis of N,N’-bis(phenoxyacetyl)hydrazines. iujp. August 2019;49(2):61-63.
Chicago 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 (August 2019): 61-63.
EndNote Apaydın ÇB, Cesur Z (August 1, 2019) A new approach for the synthesis of N,N’-bis(phenoxyacetyl)hydrazines. İstanbul Journal of Pharmacy 49 2 61–63.
IEEE Ç. B. Apaydın and Z. Cesur, “A new approach for the synthesis of N,N’-bis(phenoxyacetyl)hydrazines”, iujp, vol. 49, no. 2, pp. 61–63, 2019.
ISNAD Apaydın, Çağla Begüm - Cesur, Zafer. “A New Approach for the Synthesis of N,N’-bis(phenoxyacetyl)hydrazines”. İstanbul Journal of Pharmacy 49/2 (August 2019), 61-63.
JAMA Apaydın ÇB, Cesur Z. A new approach for the synthesis of N,N’-bis(phenoxyacetyl)hydrazines. iujp. 2019;49:61–63.
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, 2019, pp. 61-63.
Vancouver Apaydın ÇB, Cesur Z. A new approach for the synthesis of N,N’-bis(phenoxyacetyl)hydrazines. iujp. 2019;49(2):61-3.