41555-25-3

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 532-96-7 N-benzoyl-N'-phenylhydrazine 
• 67-56-1 methanol 
• 918497-00-4 α-chlorobenzaldehyde phenylhydrazone 
• 100-52-7 benzaldehyde 
• 100-63-0 phenylhydrazine 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 742-01-8 1,3,5-triphenyl-4,5-dihydro-1H-pyrazole 
• 62-53-3 aniline 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 18039-45-7 2,5-diphenyl-2H-tetrazole 
• 3815-83-6 3,4-diphenylsydnone 
• 19019-88-6 7-isopropylidene-2,3-dicarbomethoxynorbornadiene 
• 231289-36-4 C,N-Diphenylnitrilimine 

Downstream Products

• 165676-63-1 1,3-diphenyl-1H-pyrazole-4,5-dicarboxylic acid 
• 165676-62-0 1,3-diphenyl-4-carbomethoxy-5-carboxypyrazole 
• 155857-14-0 4,5-Bis-bromomethyl-1,3-diphenyl-1H-pyrazole 
• 165676-72-2 1,3-diphenyl-4-carboxy-5-amino-N-tert-butyloxycarbonylpyrazole 
• 165676-65-3 1,3-diphenyl-5-carbomethoxy-4-carboxypyrazole 
• 165676-68-6 1,3-diphenyl-4-carbomethoxy-5-isocyanato pyrazole 
• 165676-69-7 1,3-diphenyl-5-carbomethoxy-4-isocyanato pyrazole 
• 165676-64-2 anhydride du 1,3-diphenyl-4,5-dicarboxypyrazole 

Relevant academic research and scientific papers

Unexpected ring opening of pyrazolines with activated alkynes: synthesis of 1H-pyrazole-4,5-dicarboxylates and chromenopyrazolecarboxylates

1H-Pyrazole-4,5-dicarboxylates and chromenopyrazole carboxylates were prepared by reacting pyrazolines with activated alkynes under neat conditions without a catalyst. The products were formed via unexpected ring opening of pyrazolines with the elimination of styrene/ethylene. These types of transformations are unknown and the products formed were confirmed using their spectral/analytical data. In addition, the structures of compounds 5e and 5n were confirmed by single-crystal X-ray analysis. Control experiments were conducted to support the proposed reaction mechanism.

Synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides: Via a [[3 + 3] - 1] pathway

A novel and practical protocol for the synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides in excellent yields under mild conditions is described. The transformation proceeds via an unusual [[3 + 3

Preparation method of fully-substituted pyrazole derivative

The invention relates to the technical field of organic chemical synthesis, and achieves the purposes by providing a preparation method of a fully-substituted pyrazole derivative. The preparation method comprises the following steps: according to a reacti

Application of Photoclick Chemistry for the Synthesis of Pyrazoles via 1,3-Dipolar Cycloaddition between Alkynes and Nitrilimines Generated In Situ

The photochemical extrusion of gaseous nitrogen from 2,5-disubstituted tetrazoles to generate reactive nitrilimines in situ represents an efficient and attractive way to form dipoles that can be used to provide useful chemicals via 1,3-dipolar cycloadditions. The concept of “photoclick chemistry” already inspired numerous researchers, who exploited photochemical processes involving alkenes for the synthesis of adducts or the functionalization of biocompatible materials. The approach requires bioorthogonality, ease of access to the starting materials and operational simplicity. We report herein our investigations toward a photoclick reaction involving 2,5-disubstituted tetrazoles and alkynes as the dipolarophile for the synthesis of pyrazole derivatives. In addition to the numerous reports recently published on the synthesis of pyrazoles, we wish to add to the list a photochemical procedure that represents a mild and atom-economical alternative. Moreover, considering that such nitrilimines precursors can be accessed in one step from inexpensive and abundant starting materials and given the commercial availability of a broad spectrum of alkynes, we examined the scope of the photoclick reaction with respect to reactive partners, enabling the synthesis of a library of useful heteroaromatics.

Copper(ii) ionic liquid catalyzed cyclization-aromatization of hydrazones with dimethyl acetylenedicarboxylate: A green synthesis of fully substituted pyrazoles

The Lewis acid room temperature ionic liquid, [n-Bu4P][CuBr 3], was found to be an efficient and reusable catalyst for three component synthesis of fully substituted pyrazoles from the reaction of aldehydes, arylhydrazines and dimethyl acetylenedicarboxylate (DMAD). This catalytic system is simple and chemoselective with high yields.

Synthesis of 4-fluoromethylsydnones and their participation in alkyne cycloaddition reactions

We report the synthesis and some structural studies of 4-trifluoromethyl, 4-difluoromethyl-, and 4-monofluoromethylsydnones. All but the latter compounds are stable and represent effective precursors to a range of pyrazoles after cycloaddition reactions with alkynes. The cycloadditions are generally highly regioselective and provide 5-fluoromethylpyrazole products, although we have observed that Bn-substituted sydnones can provide an unexpected alkyne insertion mode that generates the 3-fluoromethyl isomer.

One-pot synthesis of functionalized 3-aryl-1-phenyl-1H-pyrazoles from hydrazonoyl chlorides and acetylenic esters in the presence of Ph3P

The zwitterionic 1 :1 intermediates generated by addition of Ph 3P to acetylenic esters is trapped by 1-[(aryl)chloromethylene]-2- phenylhydrazines (=N-phenylarenecarbohydrazonoyl chlorides) to yield functionalized 3-aryl-1-phenyl-1H-pyrazoles

SYNTHESE D'AMINO ACIDES PYRAZOLIQUES

In the field of our synthesis of heterocyclic amino acids, we describe here the preparation of two regioisomeric pyrazolic amino acids.

Dihalogentriphenylphosphoranes in Heterocyclic Synthesis; 15. A Simple One-Pot-Procedure for the Generation of Nitrilimines with the Aid of Dihalogentriphenylphosphoranes: 1,3-Dipolar Cycloadditions and 1,5-Electrocyclizations

A simple and versatile one-pot procedure for the in situ generation of nitrilimines from N-acyl hydrazines is described. 1,3-Dipolar cycloadditions and 1,5-electrocyclic ring closures are carried out.Unsymmetrically substituted dipolarophiles show typical

SITE SELECTIVITY IN THE REACTIONS OF 1,3-DIPOLES WITH NORBORNADIENE DERIVATIVES

The cycloadditions of arylazides, benzonitrile oxides and diphenylnitrile imine to norbornadiene derivatives 1a-c showed varying degree of site- and stereo-selectivity.With dipolarophile 1a arylazides and benzonitrile oxides attack, preferentially, the electron-poor tetrasubstituted double bond, while in the case of 1b and 1c is the substituted double bond which enters the cycloaddition.By contrast, 2-diazopropane and C-phenyl-N-methylnitrone react with the sole tetrasubstituted double bond of 1a-c in stereo- and site-specific cycloadditions.The quantitative evaluation of the two possible reaction paths was performed by glc analysis.The compounds detected were those arising from Diels-Alder cycloreversions of the thermally labile intermediate adducts 2 and 3 (Scheme 1).The results were rationalized on the basis of a qualitative perturbation treatment which considers frontier orbital interactions only.