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

Yıl 2019, Cilt: 49 Sayı: 2, 61 - 63, 01.08.2019

Öz

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.

Kaynakça

  • 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.
Yıl 2019, Cilt: 49 Sayı: 2, 61 - 63, 01.08.2019

Öz

Kaynakça

  • 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.
Toplam 1 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Eczacılık ve İlaç Bilimleri
Bölüm Original Article
Yazarlar

Çağla Begüm Apaydın

Zafer Cesur Bu kişi benim

Yayımlanma Tarihi 1 Ağustos 2019
Gönderilme Tarihi 11 Şubat 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 49 Sayı: 2

Kaynak Göster

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. Ağustos 2019;49(2):61-63.
Chicago Apaydın, Çağla Begüm, ve Zafer Cesur. “A New Approach for the Synthesis of N,N’-bis(phenoxyacetyl)hydrazines”. İstanbul Journal of Pharmacy 49, sy. 2 (Ağustos 2019): 61-63.
EndNote Apaydın ÇB, Cesur Z (01 Ağustos 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 ve Z. Cesur, “A new approach for the synthesis of N,N’-bis(phenoxyacetyl)hydrazines”, iujp, c. 49, sy. 2, ss. 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 (Ağustos 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 ve Zafer Cesur. “A New Approach for the Synthesis of N,N’-bis(phenoxyacetyl)hydrazines”. İstanbul Journal of Pharmacy, c. 49, sy. 2, 2019, ss. 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.