69321-29-5

Upstream product

• 69321-36-4 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-acetohydrazide 
• 103-72-0 phenyl 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 
• 89316-64-3 methyl 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetate 
• 181482-48-4 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetamide 
• 64700-15-8 7-(carboxymethoxy)-4-methylcoumarin 

Downstream Products

• 69560-70-9 7-((5-mercapto-4-phenyl-4H-1,2,4-triazol-3-yl)methoxy)-4-methyl-2H-chromen-2-one 
• 1429303-03-6 (Z)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide 

Relevant academic research and scientific papers

Synthesis of new 7-substituted 4-methylcoumarin derivatives of antimicrobial activity

New cyclic derivatives derived from 4-methyl-7-coumarinyloxyacetic acid hydrazide have been synthesized. Some representative examples were screened for antimicrobial activity.

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.

Access to new antimicrobial 4-methylumbelliferone derivatives

Synthesis of some novel coumarin esters has been accomplished through iodine-catalyzed method using 4-methylumbelliferone as the starting material. Condensation of hydrazide, which was obtained in two steps from 4-methylumbelliferone, with some arylaldhydes provided hydrazone derivatives, while the reaction with phenylthioisocyanate leads to the thiosemicarbazide that evolved into two new compounds. Finally, condensation reaction of hydrazide with three diketones afforded new pyrrole and pyrazole derivatives. Structures of all synthesized compounds were established on the basis of spectroscopic methods including 1H NMR, 13C NMR and ES-HRMS. They were finally tested for their antimicrobial activity and the structure-activity relationship was discussed.

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.

Design and synthesis of some new 1,3,4-thiadiazines with coumarin moieties and their antioxidative and antifungal activity

A series of newly disubstituted (compounds 4a,b) and trisubstituted 1,3,4-thiadiazines 5a-l with various substituents was prepared utilizing different thiosemicarbazides and 3-A-bromoacetylcoumarins as starting compounds. The structures of the synthesized

4-Methyl-7-hydroxycoumarin antifungal and antioxidant activity enhancement by substitution with thiosemicarbazide and thiazolidinone moieties

According to literature data, thiosemicarbazide and thiazolidinone moieties should enhance biological properties of coumarin. Antioxidant, metal-chelating and antifungal activities of all compounds were investigated and compared to the activity of the sta

Synthesis and Biological Activity of 1-(4-Methyl-2-oxo-2H-benzopyran-7-yloxoacetyl)-4-alkylthiosemicarbazides: 1,3-Thiadiazoles and 1,2,4-Triazoles

A series of 1-(4-methyl-2-oxo-2H-1-benzopyran-7-yloxoacetyl)-4-alkylthiosemicarbazides, S-triazoles and their methyl derivatives has been synthesized by condensation of 4-methyl-2-oxo-2H-1-benzopyran-7-yloxo-acetyl hydrazine with alkyl isothiocyanates.Subsequent ring closure of the substituted thiosemicarbazides yielded the S-triazoles and reaction with methyl iodide gave the corresponding methyl derivatives.The substituted 1,3,4-thiadiazoles have been synthesized by cyclodehydration of the substituted thiosemicarbazides with phosphoric acid.The biological activity of some new compounds is reported. - Key Words: Substituted 1,3,4-Thiadiazoles; 1,2,4-Triazoles; Biological activity.

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.