Synthesis and biological evaluation of 3-O-substituted 1-benzyl-6-oxo-1,6-dihydropyridazine derivatives

Abstract

On the basis of 2-benzyl-6-hydroxypyridazin-3(2 H)-one, a series of its novel O-substituted (including 6-(1,3,5-triazin-2-yl)oxy) derivatives is prepared. It is proven that the substitution reactions in the initial compound occur mainly at the oxygen atom of the hydroxy group. On the basis of the obtained oxy-aceto(propane)hydrazides, the corresponding azides and anilides are synthesized. A series of 2-[(1-benzyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy]- N′-(substituted benzylidene)aceto(propane)hydrazides is obtained via the reaction of various aromatic aldehydes with the same hydrazides. Heterocyclization of the latter affords compounds with a combination of pyridazine and 1,3,4-oxadiazole rings in the molecule. The reaction of oxy-acetohydrazide with potassium thiocyanate and a mixture of CS2/KOH leads to potassium salts of 2-{[(1-benzyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy]methyl}hydrazine-1-carbothioamide and 2-{2-[(1-benzyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy]acetyl}hydrazine-1-carbodithioic acid, respectively. Acid hydrolysis of the latter affords 2-benzyl-6-[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)methoxy]pyridazin-3(2 H)-one.

Design, synthesis, and antiviral activities of myricetin derivatives containing pyridazinone

“…2.2.1 General synthesis of intermediates. Intermediate 1 was synthesized using the experimental method reported in the literature, 40,41 taking 6-hydroxy-2-phenylpyridazin-3(2H)-one as an example. 1.00 g (6.92 mmol) of phenyl hydrazine hydrochloride was dissolved in 25 mL of secondary water, and heated to 90 1C until completely dissolved, then 0.75 g (7.61 mmol) of maleic anhydride was added, and 8 mL of dilute hydrochloric acid was added dropwise to the mixture, and was refluxed for 3 h. At the end of the reaction, cooled to room temperature, the mixture was poured into ice water to precipitate, left to stand, filtrated under reduced pressure and washed.…”

تشييد وتشخيص بعض المشتقات البايرازول ، ترايازول ، اوكسادايازول ، ثايازول ، ثايادايازول الحاملة لبارا- تلوين سلفونامايد الجديدة

“…The formed precipitate was filtered, washed with water and dried. 32 White solid, ( 0.43 g, 62%), m.p = 239-241°C. FT-IR ν (cm -1 ): 1091 (C=S),1155, 1342 (SO2), 1651 (C=N), 2939 (CH3), 1608 (C=C), 3321 (NH),3315 (NH ring).…”

Synthesis of Potentially Bioactive Hydrazones of Pyrimidine and 1,3,5-Triazine

“…Studies of new hydrazine derivatives are ongoing, in which compounds with antimicrobial (Masunari and Tavaris, 2007, Loncle, et al, 2004, Küҫükgüzel, et al, 2003, Vicini, et al, 2002, anti-inflammatory (Todeschini, et al, 1998), anti-tuberculosis (Bijev, 2006), antitumor (Gürsoy and Ulusoy-Güzeldemirci, 2007), antimalarial (Gemma, et al, 2006), antidepressant (Ergenҫ, et al, 1998) and anticonvulsant (Ragavendran, et al, 2007) activities have been revealed. Some hydrazide derivatives, particularly, herbicides (benquinox, saijunmao, phenoxyaryl hydrazides of nicotinic acid) (http://www.alanwood.net/ pesticides/) and also the compounds with plant growth stimulating activity (Gomktsyan, et al, 2012, Yengoyan, et al, 2017, Pivazyan, et al, 2019, Shainova, 2019 are used in agriculture.…”