306990-93-2

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 579-75-9 2-Methoxybenzoic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 37073-15-7 1-(methanesulfonyl)-1H-1,2,3-benzotriazole 

Downstream Products

• 120173-04-8 (2-methoxyphenyl)(pyrrolidin-1-yl)methanone 
• 51892-24-1 2-Methoxy-thiobenzoesaeure-S-phenylester 
• 101093-59-8 S-benzyl 2-methoxybenzenecarbothioate 
• 820234-17-1 (1H-indol-1-yl)(2-methoxyphenyl)methanone 
• 6833-21-2 2-methoxy-N-phenylbenzamide 
• 95461-02-2 N-phenyl-N'-(2-methoxybenzenecarbonyl)urea 
• 1226-63-7 1,3-bis(2-methoxyphenyl)urea 
• 13142-82-0 N-(2-methoxyphenyl)-N'-phenyl-urea 
• 60681-96-1 2-(2-methoxyphenyl)-4H-benzo[d][1,3]oxazin-4-one 
• 1043910-19-5 3-demethoxycarbonyl-3-(2'-methoxybenzoylamino)methylvindoline 
• 1043910-90-2 C₅₃H₆₃N₅O₈ 
• 1260613-32-8 1-(2-methoxybenzoyl)imidazolidin-2-one 
• 46270-50-2 1-(2-methoxyphenyl)-2-nitroethan-1-one 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

N -Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor

A diverse range of ureas, N -acylureas, carbamates, and thiocarbamates has been synthesized in good to excellent yields by reacting N -acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide (DPPA) as a suitable azide donor in anhydrous toluene at 110 °C for 3-4 hours. In this route, DPPA was found to be a good alternative to trimethylsilyl azide and sodium azide for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free conditions, straightforward nature, easy handling, use of readily available reagents, and in many cases avoidance of column chromatography are the notable features of the devised protocol.

Trichloroisocyanuric Acid Mediated High-Yielding Synthesis of N -Acylbenzotriazoles under Mild Reaction Conditions

N -Acylbenzotriazoles are achieved in good yields from the corresponding carboxylic acids by using only 0.35 equivalent of trichloroisocyanuric acid and 1.2 equivalents of PPh 3. The salient features of the developed reaction path include an ec

An Improved N-Acylation of 1 H-Benzotriazole Using 2,2′-Dipyridyl?-di?-sulfide and Triphenylphosphine

A novel path has been developed for the conversion of carboxylic acids into the corresponding N-acylbenzotriazoles by using 2,2′-dipyridyl disulfide/PPh 3 in anhydrous dichloromethane in the presence of 1 H-benzotriazole. Mild reaction conditio

Synthesis of benzotriazoles derivatives and their dual potential as α-amylase and α-glucosidase inhibitors in vitro: Structure-activity relationship, molecular docking, and kinetic studies

Benzotriazoles (4–6) were synthesized which were further reacted with different substituted benzoic acids and phenacyl bromides to synthesize benzotriazole derivatives (7–40). The synthetic compounds (7–40) were characterized via different spectroscopic techniques including EI-MS, HREI-MS, 1H-, and 13C NMR. These molecules were examined for their anti-hyperglycemic potential hence were evaluated for α-glucosidase and α-amylase inhibitory activities. All benzotriazoles displayed moderate to good inhibitory activity in the range of IC50 values of 2.00–5.6 and 2.04–5.72 μM against α-glucosidase and α-amylase enzymes, respectively. The synthetic compounds were divided into two categories “A” and “B”, in order to understand the structure-activity relationship. Compounds 25 (IC50 = 2.41 ± 1.31 μM), (IC50 = 2.5 ± 1.21 μM), 36 (IC50 = 2.12 ± 1.35 μM), (IC50 = 2.21 ± 1.08 μM), and 37 (IC50 = 2.00 ± 1.22 μM), (IC50 = 2.04 ± 1.4 μM) with chloro substitution/s at aryl ring were found to be most active against α-glucosidase and α-amylase enzymes. Molecular docking studies on all compounds were performed which revealed that chloro substitutions are playing a pivotal role in the binding interactions. The enzyme inhibition mode was also studied and the kinetic studies revealed that the synthetic molecules have shown competitive mode of inhibition against α-amylase and non-competitive mode of inhibition against α-glucosidase enzyme.

An efficient one-pot synthesis of: N, N ′-disubstituted ureas and carbamates from N -acylbenzotriazoles

A facile and high-yielding one-pot synthesis of carbamates and N,N′-disubstituted symmetrical ureas from N-acylbenzotriazoles has been devised. It is believed that, the intermediate acyl-azide undergo Curtius rearrangement and in different solvents gives different products i.e. carbamates in alcohols and N,N′-disubstituted symmetrical urea in THF.

Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents

A series of novel quinoline-oxadiazole hybrid compounds was designed based on stepwise rational modification of the lead molecules reported previously, in order to enhance bioactivity and improve druglikeness. The hybrid compounds synthesized were screened for biological activity against Mycobacterium tuberculosis H37Rv and for cytotoxicity in HepG2 cell line. Several of the hits exhibited good to excellent anti-tuberculosis activity and selectivity, especially compounds 12m, 12o and 12p, showed minimum inhibitory concentration values 500. The results of this study open up a promising avenue that may lead to the discovery of a new class of anti-tuberculosis agents.

Facile synthesis of N-acylbenzotriazoles from carboxylic acids mediated by 2,4,6-trichloro-1,3,5-triazine and triethylamine

Abstract A facile, efficient, and economic method toward N-acylbenzotriazoles was reported using 2,4,6-trichloro-1,3,5-triazine in combination with triethylamine as a carboxylic acid activator. Through reacting 1H-benzotriazole with the generated triacylated triazine intermediate, a series of N-acylbenzotriazoles could be rapidly prepared in high yields without column chromatography.

TCT-mediated synthesis of N-acylbenzotriazoles in aqueous media

The synthesis of N-acylbenzotriazoles has been demonstrated by the 2,4,6-trichloro-1,3,5-triazine (TCT)-mediated condensation of carboxylic acids with 1H-benzotriazole in aqueous media. In saturated aqueous sodium bicarbonate, TCT was found to be relatively stable and functioned as an efficient acid activator in the acyl transfer process. This operationally simple and economic method allows the scalable synthesis of N-acylbenzotriazoles in good to excellent yields.

Acyloxyphosphonium versus aminophosphonium intermediates: Application to the synthesis of N-acylbenzotriazoles

In attempts to convert carboxylic acids directly into N-acylbenzotriazoles by using Ph3P/I2 as an acid-activating system, the outcome of the reaction is reversed from no reaction to almost quantitative yield of the expected product simply by switching the order of the addition of the reagents to the presumed acyloxyphosphonium intermediate. If triethylamine was present before treatment with 1H-benzotriazole, anhydride was always exclusively generated without a detectable amount of the expected product. However, if the base was applied after the addition of 1H-benzotriazole, the reaction proceeded smoothly to afford N-acylbenzotriazoles in good to excellent yields within short reaction times. 31P NMR spectroscopy revealed the presence of a benzotriazophosphonium species in preventing the formation of the anhydride by attack of the carboxylate anion at the acyl function of the acyloxyphosphonium salt.