5955-92-0

Upstream product

• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 3623-15-2 phenyl propargyl ketone 
• 941-55-9 4-toluenesulfonyl azide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 98-86-2 acetophenone 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 150366-85-1 phenyl 1-<2-(trimethylsilyl)ethoxy>methyl-1H-1,2,3-triazol-5-yl ketone 

Downstream Products

• 103313-99-1 ethyl 2-(4-benzoyl-1H-1,2,3-triazol-1-yl)acetate 
• 103314-01-8 2-carbethoxymethyl-4-benzoyl-2H-1,2,3-triazole 
• 103314-18-7 (3-nitrophenyl)(1H-1,2,3-triazol-4-yl)methanone 

Relevant academic research and scientific papers

Rational design and synthesis of yellow-light emitting triazole fluorophores with AIE and mechanochromic properties

Previously, we reported that N-2-aryl triazoles (NATs) exhibited good fluorescence activity in the UV/blue light range. In an effort to achieve biocompetitive NAT fluorophores with green/yellow emission, a new class of 4-keto-2-(4′-N,N-diphenyl)-phenyl triazoles were designed and synthesized. Herein, we present our study on these novel fluorophores which demonstrated excellent luminescence emission both in solution (Φ up to 96%) and in the solid state (Φ up to 43%). Furthermore, these new compounds showed aggregation-induced emission (AIE) properties and reversible mechanochromic luminescence properties, which suggested their potential applications in chemical and materials science.

Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide

The synthesis of 4-acyl-NH-1,2,3-triazoles has been accomplished with high efficiency through the cycloaddition reactions between N,N-dimethylenaminones and tosyl azide. This method is featured with extraordinary sustainability by employing water as the s

Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks

Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.

Reactions of β-azolylenamines with sulfonyl azides as an approach to N-unsubstituted 1,2,3-triazoles and ethene-1,2-diamines

The reactions of β-azolylenamines 1 with sulfonyl azides 2 in acetonitrile furnished 1H-4-(azol-5-yl)-1,2,3-triazoles 3 in yields of 52-93%. β-Benzoylenaminones and β-nitroenamine of type 1 also reacted with tosyl azide to form the same type of products 3, proving the generality and efficiency of the method for the synthesis of N-unsubstituted 1,2,3-triazoles. On the other hand, the reactions of 3-(1-aryl-1,2,3-triazol-5-yl)enamines with tosyl azide in the absence of a solvent afforded a mixture of (E)-1-dimethylamino-2-tosylaminoethenes 5 and N,N-dimethyl-N′- tosylformamidine 6 in yields of 40-50 and 20%, respectively. The formation of a variety of compounds from the reactions of enamines 1 with sulfonyl azides 2 is rationalized by the various possible transformations of the intermediate 5-dimethylamino-1,2,3-triazolines 7.

A convenient synthesis by microwave heating and pharmacological evaluation of novel benzoyltriazole and saccharine derivatives as 5-HT1A receptor ligands

A series of novel 1,2,3-4-benzoyltriazole and saccharine derivatives were designed and synthesized by microwave heating. They were evaluated on a battery of receptors, including serotonin 5-HT1A, 5-HT2A and 5-HT2C, and the most interesting compounds were further evaluated on dopaminergic D1, D2 and adrenergic α1, α2 receptors. Conventional and microwave heating of the reactions were compared. Synthesis by microwave heating gave the desired compounds in better yields than those obtained by conventional heating. The overall times for the syntheses were considerably reduced. All compounds displayed moderate affinity for 5-HT1A receptor. The most interesting compound 33 showed a high affinity (Ki=93 nM) which was combined with no affinity on the other receptors considered.

Preparation and local anaesthetic activity of benzotriazinone and benzoyltriazole derivatives

Two sets of benzotriazinone and benzoyltriazole derivatives were prepared and tested for local anaesthetic activity in comparison with lidocaine. Several of the prepared compounds exhibited a fairly good activity comparable or superior to that of lidocaine. The presence of a benzotriazinone or a benzoyltriazole moiety as an aromatic system was quite profitable for both the intensity and duration of activity. The acute toxicity in mice of the four most potent compounds of the series was also assessed. Compound 1b, which has an anaesthetic activity comparable to that of lidocaine, was also characterized by a more favourable therapeutic index. All compounds were tested in vitro to evaluate their negative chronotropic action in isolated rat right atria.

Synthesis and binding affinities for 5-HT(1A), 5-HT(2A) and 5-HT(2C) receptors of a series of 1- and 2-(4-arylpiperazinylalkyl)-4-(benzoyl)-1,2,3- triazole derivatives

A number of 1- and 2-(4-arylpiperazinylalkyl)-4-(benzoyl)-1,2,3-triazole derivatives (1-4) were prepared in order to obtain compounds with a high affinity and selectivity for 5-HT(1A) receptors. 5-HT(1A), 5-HT(2A) and 5- HT(2C) affinities were determined by radioligand binding experiments and the most active compounds were also tested for binding affinities on dopaminergic D-1, D-2 and adrenergic α1, α2 receptors. The modification of aromatic substituents, the length of the alkyl chain and its position on the 4- benzoyl-1,2,3-triazole ring were explored. Most of the considered compounds generally showed moderate to high affinity for the 5-HT(1A) receptor binding site. Three derivatives 2c, 3c and 3e bind to 5-HT(1A) receptors in the nanomolar range (IC50 values = 2, 7.2 and 2.6 nM respectively). The most active compound, 2c, presented a high degree of selectivity versus all considered receptors. It was found that the benzoyltriazole derivatives 1h and 4c are new selective ligands for 5-HT(2A) (IC50 = 89 nM) and 5-HT(2C) receptors (IC50 = 17 nM), respectively.

Functionalisation of 1,2,3-Triazole via Lithiation of 1-methyl-1H-1,2,3-triazole

The preparation of a number of 5-substituted 1-methyl-1H-1,2,3-triazoles via reaction of 1-methyl-1H-1,2,3-triazole with n-butyllithium followed by addition of various electrophiles is reported.Removal o