in Wiley Online Library (wileyonlinelibrary.com).The synthesis of some triazolotriazine, tetrazolotriazine, triazinotetrazine, and triazinotetrazepinoindole by the reaction of 4-amino-6-benzyl-3-hydrazinyl-1,2,4-triazin-5(4H)-one (2) with different reagents is described. The synthesized compounds were screened for their antimicrobial activity using the minimum inhibition concentration method by serial dilution technique. Two of these compounds showed higher activity than that of standard drug, and they were further evaluated for their cytotoxic activities against human cancer cells (MCF-7, HCT116, and HepG2), which indicate strong effect on these cancer cell lines. J. Heterocyclic Chem., 55, 971 (2018). and the carbonyl group of acid to form hydrazone intermediate, which underwent a cyclization reaction between the secondary amine and the hydroxyl group of the acid function affording 3, following pathway A. The constitution of 3 was deduced from its spectral data. Its 1 H NMR spectrum showed a singlet signal at δ = 2.49 and 6.05 ppm corresponding to CH 3 and NH 2 , Scheme 2. Action of 1,2-diketonic compounds on the triazino hydrazine derivative 2 to form the corresponding hydrazones 7, 8, 9, and 11. Scheme 1. Heterocyclization reaction of 2 with various reagents. Scheme 3. Alkylation of hydrazine derivative 2 with halo compounds.
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This review summarizes results from a literature survey concerning the synthesis and reactions of 4-amino-3-mercapto-1,2,4-triazine-5-ones reported by research groups from 1983 to mid. 2015.
The chemical reactivity of 4‐amino‐6‐benzyl‐3‐mercapto‐1,2,4‐triazine‐5(4H)‐one (1) towards various aliphatic or/and mono and bis aromatic carboxylic acid derivatives to give the corresponding fused heterocyclic systems, 1,3,4‐thiadiazoles 4, 5, 6, which incorporating 1,2,4‐triazine nucleus was achieved. Moreover, compound 1 was subjected to react either with halo acetic acids or bromo ester to afford the respective fused nitrogen ring junction systems, thiadiazole 2 and 3, or thiadiazine 7. However, the tetracyclic ring system 9 was furnished through condensation reaction of isatine with triazine 1. In addition, some of the new synthesized compounds were evaluated as an antioxidant and antitumor agents.
A new series of 1,2,4‐triazine derivatives were designed, synthesized, and identified on the basis of IR, 1H‐NMR, 13C‐NMR, and EI‐MS spectral data. The potent acaricidal activity of 1,2,4‐triazine derivatives against eggs and adult female of Tetranychus urticae (Koch) was assessed compared with pyridaben under laboratory conditions. Structure acaricidal activity relationships of the promising 1,2,4‐triazine derivatives were analyzed for eggs and adult female; the nature and position of the substituents were important in demonstration of the activities.
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