69560-75-4

Upstream product

• 69321-34-2 N-(4-methoxyphenyl)-2-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)hydrazinecarbothioamide 
• 69321-36-4 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-acetohydrazide 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 5614-82-4 ethyl 2-(4-methyl-2-oxo-2-coumarin-7-yloxy)acetate 

Relevant academic research and scientific papers

Choline Chloride Based Deep Eutectic Solvents as a Tuneable Medium for Synthesis of Coumarinyl 1,2,4-Triazoles: Effect of Solvent Type and Temperature

A study of 1,2,4-triazole synthesis from 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide (1) or 2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetohydrazide (2) and various isothiocyanates, in deep eutectic solvents, was performed. In order to find the best conditions for 1,2,4-triazole formation, a model reaction on 1 and phenylisothiocyanate was performed in 14 different choline chloride based deep eutectic solvents, at two different temperatures (40 °C and 80 °C). Pure 1,2,4-triazoles were obtained in choline chloride/urea (1:2) and choline chloride/N-methyl urea (1:3) deep eutectic solvents at 80 °C. Pure thiosemicarbazides were obtained in choline chloride/ethane-1,2-diol (1:2), choline chloride/malic acid (1:1), choline chloride/malonic acid (1:1), choline chloride/butane-1,4-diol (1:3) and choline chloride/glycerole (1:2) at 40 °C. The ratio of 1,2,4-triazoles and thiosemicarbazides in reaction mixtures was determined by HPLC and 1H NMR. After the best conditions for 1,2,4-triazole synthesis were found, some coumarinyl 1,2,4-triazoles were synthesized from two different coumarinyl hydrazides (1 and 2) and various alkyl and aryl isothiocyanates in one step reaction.

Synthesis and antimicrobial activities of some triazole, thiadiazole, and oxadiazole substituted coumarins

Ethyl-2-(4-methyl-2-oxo-2-coumarin-7-yloxy)acetate 1 has been prepared from 7-hydroxy-4-methyl-2-coumarin, which on further treatment with hydrazine hydrate in boiling ethanol gave the hydrazide compound 2. The resulting hydrazide was reacted with substituted aryl isothiocyanates to form thiosemicarbazides compounds 3a, 3b, 3c, 3d, 3e. 1-(2-(4-Methyl-2-oxo-2- coumarin-7-yloxy)acetyl)-4-aryl thiosemicarbazides 3 underwent cyclization with different reagents under different reaction conditions to furnish coumarin derivatives possessing triazoles 4a, 4b, 4c, 4d, 4e, thiadiazoles 5a, 5b, 5c, 5d, 5e, and oxadiazoles 6a, 6b, 6c, 6d, 6e, respectively. The structures of all the compounds have been assigned by elemental analysis and spectral studies. The synthesized compounds were screened for their antimicrobial analgesic activities. The nonconventional controlled microwave irradiation synthesis is carried out at (200 W) at 70°C. This approach offers a number of advantages in terms of methodology, high-product yield, short reaction time, mild reaction conditions, environmentally benign, and easy workup.

Synthesis of substituted coumarinyloxy triazoles and thiadiazoles and their antimicrobial activity

Hydrazides and thiosemicarbazides of substituted coumarins have been synthesised by condensing substituted carbethoxy coumarins with hydrazine hydrate and aryl isothiocyanates respectively.The thiosemicarbazides when cyclised on treatment with NaOH and conc.H2SO4 give triazoles and thiadiazoles.The synthesised compounds have been tested for their anti-microbial activity against Alternaria brassicicola, Fusarium udam, Staphylococcus gram (-ve), Lactobacilus gram (-ve).However none of them show any significant activity.