Syntheses of 1-(4-methylsulfonylphenyl)-5-aryl-1,2,3-triazoles and -(4-aminosulfonylphenyl)-5-aryl-1,2,3-triazoles

Daha, Fariba Johari; Matloubi, Hojatollah; Tabatabi, S. A.; Shafii, B.; Shafiee, Abbas

doi:10.1002/jhet.5570420106

Cited by 9 publications

(4 citation statements)

References 8 publications

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“…Shafii and co-workers 181 reported the synthesis of 1-(4-aminosulfonylphenyl)-5-aryltriazoles and 1-(4-methylsulfonylphenyl)-5-aryltriazoles 359 as COX-2 inhibitors. First, they prepared an imino compound 357 by the reported method, 182 but it did not work.…”

Section: Metal-free Synthesis Of 123-triazolementioning

confidence: 99%

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Vala

Patel

2022

ACS Omega

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1,2,3-Triazole scaffolds are not obtained in nature, but they are still intensely investigated by synthetic chemists in various fields due to their excellent properties and green synthetic routes. This review will provide a library of all synthetic routes used in the past 21 years to synthesize 1,2,3-triazoles and their derivatives using various metal catalysts (such as Cu, Ni, Ru, Ir, Rh, Pd, Au, Ag, Zn, and Sm), organocatalysts, metal-free as well as solvent- and catalyst-free neat syntheses, along with their mechanistic cycles, recyclability studies, solvent systems, and reaction condition effects on regioselectivity. Constant developments indicate that 1,2,3-triazoles will help lead to future organic synthesis and are useful for creating molecular libraries of various functionalized 1,2,3-triazoles.

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Section: Metal-free Synthesis Of 123-triazolementioning

confidence: 99%

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Vala

Patel

2022

ACS Omega

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“…Herein, as part of our ongoing program to design novel selective COX‐2 inhibitors , we describe the synthesis of a novel class of 1,5‐diarylimidazole‐2‐thiones, which for some derivatives need some modifications in standard procedures.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Approaches towards the Sulfonamide Substituted‐1,5‐Diarylimidazole‐2‐thiones as Selective Cyclooxygense‐2 inhibitors

Navidpour

Amini

Miri

et al. 2013

Journal of Heterocyclic Chem

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A new series of sulfonamide substituted 1,5‐diarylimidazole, possessing C‐2 alkylthio moiety, were synthesized for their cyclooxygense‐2 (COX‐2) inhibitory activity starting from condensation of N,N‐dibenzylaminosulfonylphenacylamine hydrochloride (2) and corresponding isothiocyanate in the presence of Et3N, followed by alkylation in the basic medium. In concomitant with these intermediates, 2‐arylamino‐5‐arylthiazole derivatives 5 were also produced. The ratio of these two products was variable with different isothiocyanates. Final debenzylation was achieved using concentrated sulfuric acid to give the title sulfonamides 8.

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“…Besides, synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives have a great deal of importance because of their broad spectrums of biological characteristics such as anti-inflammatory, anti-fungal and anti-bacterial activities [6][7][8][9][10][11][12][13]. As an extension of our previous work on the synthesis of small bioactive heterocyclic molecules [14][15][16][17], we wish to report the synthesis of 5-[(2-methyl-5-nitro-1H-imidazole-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione (10) and its methyl and ethyl thioacetate derivatives 11a-b, and N-substituted 2-amino-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-thiadiazoles (13a-f) as possible effective antimicrobial drugs. …”

Section: Introductionmentioning

confidence: 99%

Convenient syntheses of 5‐[(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl]‐1,3,4‐oxadiazole‐2(3H)thione and N‐substituted 2‐amino‐5‐[(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl]‐1,3,4‐thiadiazoles

Mirzaei

Pirelahi

Amini

et al. 2008

Journal of Heterocyclic Chem

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Oxidation of metronidazole (4) with sodium dichromate yielded the corresponding 2‐(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)acetic acid (5) which was esterified with 1‐butanol to give butyl 2‐(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)acetate (8). Reaction of the latter with hydrazine hydrate gave 2‐(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)acetohydrazide (9). Compound 5‐[(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl]‐1,3,4‐oxa‐diazole‐2(3H)‐thione (10) could be obtained through the reaction of compound 9 with carbon disulfide in basic medium. Subsequent alkylation of compound 10 afforded alkyl 2‐(5‐[(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl]‐1,3,4‐oxadiazol‐2‐ylthio)acetate (11) in good yield. Reaction of hydrazide 9 with substituted isothiocynate yielded 1‐[2‐(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)acetyl]‐4‐aryl(or ethyl)thiosemicarbazide (12) which was cyclized in acidic media to N‐substituted 2‐amino‐5‐[(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl]‐1,3,4‐thiadiazole (13).

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Syntheses of 1-(4-methylsulfonylphenyl)-5-aryl-1,2,3-triazoles and -(4-aminosulfonylphenyl)-5-aryl-1,2,3-triazoles

Cited by 9 publications

References 8 publications

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Synthetic Approaches towards the Sulfonamide Substituted‐1,5‐Diarylimidazole‐2‐thiones as Selective Cyclooxygense‐2 inhibitors

Convenient syntheses of 5‐[(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl]‐1,3,4‐oxadiazole‐2(3H)thione and N‐substituted 2‐amino‐5‐[(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl]‐1,3,4‐thiadiazoles

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