52039-87-9Relevant academic research and scientific papers
Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ
Zheng, Yuanqin,Zhou, Yuqiao,Zhang, Yan,Deng, Pengchi,Zhao, Xiaohu,Jiang, Shichao,Du, Guangxi,Shen, Xin,Xie, Xinyu,Su, Zhishan,Yu, Zhipeng
, (2021/12/22)
Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.
One-pot and novel route for the synthesis of 4-substituted-1,2,4- triazolidine-3,5-diones
Ghorbani-Choghamarani, Arash,Nikoorazm, Mohsen,Azadi, Gouhar
, p. 451 - 454 (2014/03/21)
The efficient and one-pot synthesis of 4-substituted-1,2,4-triazolidin-3,5- dione derivatives (4-substituted urazoles) via combination of triphosgene, substituted anilines, and ethyl carbazate in the presence of cesium carbonate is presented.
N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines in heterocyclic synthesis. part IX.* novel triazolo-fused thiatriazoles and pyrazolo-fused oxathiazines
Forsyth, Craig M.,Francis, Craig L.,Jahangiri, Saba,Liepa, Andris J.,Perkins, Michael V.,Young, Anna P.
, p. 785 - 791 (2011/07/31)
N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with 4-substituted urazoles 2 to give [1,2,4]triazolo[1,2-b] [1,2,3,5]thiatriazoles 3 in a selective 1,2-NN dinucleophilic mode of reaction.The reaction of 1 with N1-substituted pyrazol-5-ones 4 afforded pyrazolo[4,3-e][1,4,3] oxathiazines 5 via selective 1,3-CCO dinucleophilic substitution. Compounds 3 and 5 were the sole products isolated from the respective reactions and both represent new ring systems. CSIRO 2010.
Synthesis and anti-leishmanial activity of heterocyclic betulin derivatives
Alakurtti, Sami,Heiska, Tuomo,Kiriazis, Alexandros,Sacerdoti-Sierra, Nina,Jaffe, Charles L.,Yli-Kauhaluoma, Jari
experimental part, p. 1573 - 1582 (2010/05/02)
Betulin, a naturally occurring abundant triterpene is converted in four steps to 3,28-di-O-acetyllupa-12,18-diene. When various 4-substituted urazoles were oxidized to the corresponding urazines with iodobenzene diacetate in the presence of 3,28-di-O-acetyllupa-12,18-diene, new heterocyclic betulin derivatives were produced. These betulin derivatives were examined in a microplate assay at 50 μM for their ability to inhibit the growth of Leishmania donovani axenic amastigotes, a species that causes the fatal visceral leishmaniasis. GI50 (concentration for 50% growth inhibition) values of the most effective compounds were determined and their cytotoxicity on the human macrophage cell line THP-1 evaluated. The anti-leishmanial activity on L. donovani amastigotes growing in macrophages was also examined. The heterocycloadduct between 3,28-di-O-acetyllupa-12,18-diene and 4-methylurazine was the most effective derivative with an GI50 = 8.9 μM against L. donovani amastigotes.
Novel and efficient synthesis of 4-substituted-1,2,4-triazolidine-3,5- diones from anilines
Mallakpour, Shadpour,Rafiee, Zahra
, p. 1927 - 1934 (2008/02/04)
A simple and efficient three-step synthetic procedure for the preparation of 4-substituted phenyl derivatives of 1,2,4-triazolidindiones (urazoles), starting from anilines, has been developed. In this method, aniline derivatives were reacted with 4-nitrophenyl chloroformate to provide corresponding carbamate derivatives. In the second step, semicarbazide derivatives were prepared from these carbamates by reaction with ethyl carbazate. The cyclization reaction of corresponding semicarbazides furnished 1,2,4-triazolidindiones in high yields. Copyright Taylor & Francis Group, LLC.
A novel one-pot synthesis of 4-substituted 1,2,4-triazolidine-3,5-diones
Mallakpour, Shadpour,Rafiee, Zahra
, p. 1255 - 1256 (2007/12/26)
A simple and one-pot pathway for the preparation of 4-substituted phenyl derivatives of triazolidindiones (urazoles), starting from aniline derivatives is reported. In these methods aniline derivatives were reacted with ethyl chloroformate, to give the corresponding carbamate derivatives. In the second step semicarbazide derivatives were prepared from these carbamates by reaction with ethyl carbazide. The cyclization reactions of the corresponding semicarbazides furnished triazolidindiones. All reactions were performed in one vessel without the isolation of reaction intermediates, such as carbamates and semicarbazides, and the final products were isolated in good yields. Georg Thieme Verlag Stuttgart.
Proton-Transfer Chemistry of Urazoles and Related Imides, Amides, and Diacyl Hydrazides
Bausch, M. J.,David, B.,Dobrowolski, P.,Guadalupe-Fasano, C.,Gostowski, R.,et al.
, p. 5643 - 5651 (2007/10/02)
Equilibrium acidity constants have been determined for 1,2,4-triazolidine-3,5-dione (urazole), several substituted urazoles, and other related acids, in both dimethyl sulfoxide (DMSO) and aqueous solution.In DMSO, urazole has a pKa of 13.1.In w
1,2-Alkylene-4-substituted urazole herbicides
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, (2008/06/13)
Disclosed is a novel 1,2-alkylene-4-substituted urazole derivative which has unique biological activities, especially a herbicidal or weeding activity.
