- Reaction of Metallo S-Alkyl N-Cyanodithioiminocarbonates and Alkyl N-Cyanocarbamates with Hydrazine. A Novel Preparation of 5-Amino-3-mercapto-1,2,4-triazole
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Metal salts of S-alkyl-N-cyanodithioiminocarbonates 7 react as electrophiles with hydrazine hydrate to form 5-amino-3-mercapto-1H-1,2,4-triazole 1. The novel 4-cyanothiosemicarbazide 9 is proposed as the intermediate which cyclizes to the aromatic triazole. The rate determining step is addition of hydrazine to the iminocarbonate and is second order. Other nucleophiles such as substituted hydrazines and amines failed to react. Exchange of either or both sulfurs with oxygen leads to decomposition or mixtures of products.
- Marble, Lyndon K.,Puckett, Wallace E.,Summers, William Russell
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- First novel synthesis of triazole thioglycosides as ribavirin analogues
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This study reports a novel and efficient method for the synthesis of the first reported novel class of triazole thioglycosides. These series of compounds were designed through the reaction of potassium cyanocarbonimidodithioate 2 with hydrazine derivatives 3a-d in EtOH at room temperature to give the corresponding potassium 5-amino-1H-1,2,4-triazole-3-thiolates 4a-d. The latter compounds were treated with tetra-O-acetyl-α-D-glucopyranosyl bromide 6a and tetra-O-acetyl-α-D-galactopyranosyl bromide 6b in DMF at room temperature to give in high yields the corresponding triazole thioglycosides 7a-h. Treatment of triazole salts 4a–d with hydrochloric acid afforded the corresponding 3-mercaptotriazoles 5a-d. Compounds 5a-d were then reacted with bromoperacetylated sugars 6a,b in sodium hydride-DMF at ambient temperature to afford the thioglycosyl compounds 7a-h. Ammonolysis of the triazole thioglycosides 7a-h afforded the corresponding free thioglycosides 8a-h. The scope and limitation of the method is demonstrated. The structure of the reaction products was confirmed on the basis of their elemental analysis and spectral data (IR, 1H NMR, MS and 13C NMR).
- Elgemeie, Galal H.,Abu-Zaied, Mamdouh A.,Nawwar, Galal A.
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p. 112 - 123
(2018/02/09)
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- Synthesis, structures, catalytic, and anticancer activities of some coordination compounds involving two new triazole derivatives
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Five N-heterocyclic carboxylate-based coordination complexes, [Co(L1)2(H2O)2]·2H2O (1), [Cd(L1)2(H2O)2]·2H2O (2), [Co(L2)(H2O)3] (3), [Ni(L2)(H2O)3] (4), and [Cu2(L2)2(H2O)2] (5), have been synthesized and characterized by elemental analysis, IR spectroscopy, Powder X-ray diffraction, thermogravimetric analyses, and single-crystal X-ray crystallography, where HL1 is 2-((5-amino-1H-1,2,4-triazol-3-yl)thio)acetic acid and H2L2 is 2-((5-amino-1-(carboxymethyl)-1H-1,2,4-triazol-3-yl)thio)acetic acid. In these complexes, the hydrogen bonds (H-bonds) play an important role in their packing structures. Complex 1 has nine H-bonds showing a 3-D sqc38 topology. Complex 2 has 17 H-bonds exhibiting a 3-D hxl network. Complexes 3 and 4 are isomorphic, both of which possess ten H-bonds to present a 3-D btc topology. Complex 5 with eight H-bonds forms a 2-D sq1 structure. In addition, complex 3 catalyzes the decolorization of methyl orange. Meanwhile, 1, 3, and 5 show certain anticancer activities to inhibit the growth of HepG2 cells.
- Xiao, Dan,Yu, Ying-Hui,Wang, Zi-Shi,Yu, Chun-Hui,Hou, Guang-Feng,Chen, Yan-Mei,Gong, Xian-Feng,Ma, Dong-Sheng,Gao, Jin-Sheng
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p. 2225 - 2239
(2015/07/15)
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- Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: Derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety
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A series of novel 1,3,4-thiadiazole derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety were synthesized by the method of splicing active substructures. Among these derivatives, compounds 12, 13, 15-22 and 24-31 were firstly reported. All the compounds were assayed for antimicrobial activities against five fungi strains and four bacteria strains. The preliminary results indicated that compounds 25 and 28-31 showed good antifungal activities against Physaclospora piricola and Rhizoctonia solani. Compound 26 exhibited good antifungal activities against Cercospora beticola and R. solani. Most of the compounds showed better antibacterial activities against Gram-negative bacteria strains than Gram-positive bacteria strains. Compounds 25 and 28 showed the best activities against Pseudomonas fluorescence while compounds 30-31 showed good activities against Escherichia coli.
- Luo, Yin,Zhang, Shuai,Liu, Zhi-Jun,Chen, Wu,Fu, Jie,Zeng, Qing-Fu,Zhu, Hai-Liang
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- Synthesis and antifungal evaluation of 1,2,4-triazolo[1,5-α] pyrimidine bearing 1,2,4-triazole heterocycle derivatives
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In order to search novel fungicides with higher activity, 28 new 1,2,4-triazolo[1,5-α]pyrimidine derivatives bearing 1,2,4-triazole heterocycle were synthesized. Their structures were characterized by 1H NMR spectroscopy, mass spectrometry and elemental analyses. With triadimefon, validamycin and carbendazim as positive controls, the antifungal activities of 28 compounds against Fusarium oxysporum f. sp. vasinfectum, Gibberella sanbinetti, Cercospora beticola Sacc., Physaclospora piricola and Rhizoctonia solani were evaluated. Compound 2-[(5-(2,6- difluorobenzylthio)-4- phenyl-4H-1,2,4-triazol-3-yl)methylthio]-5,7-dimethyl[1,2,4]triazolo[1, 5-α]pyrimidine (19) showed potent antifungal activities against G. sanbinetti, C. beticola, P. piricola and R. solani. On the basis of the biological results, structure-activity relationships of these compounds were also discussed.
- Chen,Xiang,Fu,Zeng,Zhu
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p. 602 - 608
(2012/01/02)
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- Process for the preparation of 3-mercapto-5-amino-(1H)-1,2,4-triazole
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3-Mercapto-5-amino-(1H)-1,2,4-triazole is prepared by the rearrangement of 2,5-diamino-1,3,4-thiadiazole. The rearrangement proceeds in high yields under aqueous alkaline conditions.
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- Addition-Cyclisations of Ethoxycarbonyl Isothiocyanate with Hydrazine Derivatives as a Source of Thiadiazoles and Triazoles
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Ethoxycarbonyl isothiocyanate reacts additively with hydrazine, ethoxycarbonylhydrazine, as well as amino- and 1,2-diaminoguanidine.Simultaneous or subsequent cyclisation of the resulting 1:1- or 2:1-adducts in acidic or alkaline media yields substituted 1,3,4-thiadiazoles or 1,2,4-triazoles, respectively.
- Kurzer, Frederick,Secker, Jane L.
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p. 355 - 360
(2007/10/02)
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