18076-30-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 3370, 1978 DOI: 10.1021/jo00411a023Tetrahedron Letters, 9, p. 281, 1968

InChI:InChI=1/C21H16N2/c1-4-10-16(11-5-1)19-20(17-12-6-2-7-13-17)22-23-21(19)18-14-8-3-9-15-18/h1-15H,(H,22,23)

Upstream product

• 54799-83-6 3,4,5-triphenyl-pyrazole-1-carboxylic acid methyl ester 
• 536-74-3 phenylacetylene 
• 908093-98-1 diazodiphenylmethane 
• 24108-44-9 3,5,6-triphenyl-[1,2,4]triazine 
• 67-68-5 dimethyl sulfoxide 
• 99939-05-6 3,4,5-Triphenyl-1H-pyrazol-1-amin 
• 39672-37-2 4,5,6-triphenyl-1,2,3-triazine 
• 64-17-5 ethanol 
• 62398-10-1 2-acetoxy-2-phenylacetophenone 
• 4888-39-5 1,2,3-triphenylpropane-1,3-dione 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 2510-95-4 2,3-diphenylacrylonitrile 
• 119-61-9 benzophenone 

Downstream Products

• 33314-42-0 4,4',4''-(1H-pyrazole-3,4,5-triyl)-tris-aniline 
• 108159-70-2 bis(3,4,5-triphenylpyrazol-1-yl)diazene 
• 33314-43-1 4-(4-bromo-phenyl)-3,5-diphenyl-1H-pyrazole 
• 99939-05-6 3,4,5-Triphenyl-1H-pyrazol-1-amin 
• 33314-49-7 3,4,5,3',4',5'-hexaphenyl-1H,1'H-1,1'-carbonyl-bis-pyrazole 
• 33314-41-9 3,4,5-tris-(4-nitro-phenyl)-1H-pyrazole 
• 33314-39-5 1-ethyl-3,4,5-triphenyl-1H-pyrazole 
• 33314-38-4 1-methyl-3,4,5-triphenyl-1H-pyrazole 
• 33314-40-8 1-(2-bromo-ethyl)-3,4,5-triphenyl-1H-pyrazole 
• 33314-51-1 3,4,5,3',4',5'-hexaphenyl-1H,1'H-1,1'-ethane-1,2-diyl-bis-pyrazole 

Relevant academic research and scientific papers

Synthesis of 3H-pyrazoles by reaction of methyl and p-tolyl phenylethynyl sulfones with diphenyldiazomethane and their thermal and acid-catalyzed transformations

Methyl and p-tolyl phenylethynyl sulfones reacted with diphenyldiazomethane in diethyl ether at 20° C to give 1,3-dipolar cycloaddition products both according and contrary to the von Auwers rule, sulfonyl-substituted 3H-pyrazoles at a ratio of 1 : 1.5 and 1.3 : 1, respectively. On heating in toluene for 2 h, the Auwers adducts underwent van Alphen-Hüttel rearrangement with 1,5-sigmatropic shift of one phenyl substituent to afford sulfonyl-substituted 4H-pyrazoles. Under analogous conditions, the anti-Auwers adducts rearranged into sulfonyl-substituted N-phenyl-1H-pyrazoles containing a small amount of the denitrogenation product, sulfonyl-substituted cyclopropene. The Auwers adducts, as well as 4H-pyrazoles resulting from their thermal rearrangement, were converted in 5-7 days at 20°C into 3,4,4-triphenyl-1H-pyrazol-5(4H)-one by the action of a catalytic amount of sulfuric acid in acetic acid. Under analogous conditions, the regioisomeric anti-Auwers adducts gave rise to 3,4,5-triphenyl-1H-pyrazole with an impurity of 4-(R-sulfonyl)-1,3,5-triphenyl-1H-pyrazoles.

Similarity and Differences in the Regioselectivities of Thermal and Acid-Catalyzed van Alphen–Hüttel Rearrangements in the Series of 3,3-Diphenyl-3H-pyrazoles Containing Electron-Withdrawing Substituents on C4 and C5

3,3-Diphenyl-3H-pyrazoles containing an electron-withdrawing substituent in the 5-position undergo van Alphen–Hüttel rearrangement with migration of one phenyl group to C4 on heating in an aprotic solvent (benzene, toluene), as well as on keepi

Y(OTf)3-Catalyzed Cascade Propargylic Substitution/Aza-Meyer-Schuster Rearrangement: Stereoselective Synthesis of α,β-Unsaturated Hydrazones and Their Conversion into Pyrazoles

A straightforward and concise method for the highly stereoselective synthesis of α,β-unsaturated hydrazones by the Y(OTf)3-catalyzed cascade propargylic substitution/aza-Meyer-Schuster rearrangement reaction of tertiary propargylic alcohols and

Functionalized pyrazoles as agents in C-C cross-coupling reactions

The 1-tetrahydropyranyl-(THP-)protected pyrazoles 4-R-pz(THP) (R=pinacolatoboryl=Bpin (3a(THP)), Me3Si (4a(THP)), Me3Sn (5a(THP)), and 4-R-3,5-Ph2pz (R=Bpin (3b(THP)), Me3Si (4b(THP)), Me3Sn (5b(THP))

One-pot synthesis of pyrazoles through a four-step cascade sequence

A one-pot synthesis of 3,4,5- and 1,3,5-pyrazoles from tertiary propargylic alcohols and para-tolylsulfonohydrazide has been accomplished. The pyrazoles are formed through a four-step cascade sequence, including FeCl 3-catalyzed propargylic substitution, aza-Meyer-Schuster rearrangement, base-mediated 6πelectrocyclization, and thermal [1,5] sigmatropic shift. In this reaction, the 3,4,5- and 1,3,5-pyrazoles are produced selectively according to different substituents in the starting alcohols. A one-pot recipe: The synthesis of 3,4,5- and 1,3,5-pyrazoles from tertiary propargylic alcohols and para-tolylsulfonohydrazide has been accomplished. The pyrazoles are formed through a four-step cascade sequence (see figure), and are produced selectively according to different substituents in the starting alcohols.

NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS

Nitrogen-containing heterocyclic compounds represented by the following Formula (1) are provided. The compounds or salts thereof have a strong EP1 antagonistic activity when they are administered to a human or an animal, and they are useful as an effective component of a pharmaceutical agent for prophylaxis and/or treatment of an overactive bladder, for example. Furthermore, they are useful as an effective component of a pharmaceutical agent for the prophylaxis and/or treatment of symptoms including frequent urination, urinary urgency and urinary incontinence.

Thermal and acid-catalyzed transformations of 3H-pyrazoles obtained from diphenyldiazomethane and methyl phenylpropiolate

Reaction of diphenyldiazomethane with methyl phenylpropiolate in diethyl ether alongside the expected methyl triphenyl-3H-pyrazole-4-and-5-carboxylates (I and II) (38 and 24%) gave rise also to 8% of methyl 3,5-diphenyl-1-(1- ethoxyethyl)-1H-pyrazole-4-ca

Photochemistry of N-heterocycles, 5: A comparison of chemical and photochemically induced reduction of some 2(4),5-dihydro-1,2,4-triazines and aromatic 1,2,4-triazines

Chemical reduction (Zn/AcOH) of the arene 1 and of 2(4),5-dihydro-1,2,4- triazine 7 has been reinvestigated, resulting in the amendment of literature data concerning this reaction. Chemical, electrochemical, and photochemically induced reductions and ring contractions of 1,2,4-triazine derivatives have been compared. The first example of a triaryl-1,4-dihydrotriazine has been prepared. Some further evidence is presented that supports the proposed mechanism of the photochemically induced reduction and ring contraction of 1,2,4-triazines.

Photochemistry of N-Heterocycles. Part 3. Synthesis and Photochemistry of some New Dihydro-1,2,4-triazines and their Quaternary Salts

Several new dihydro-1,2,4-triazines, 1b, 4, 5, 16 and 19, have been synthesized and their structures unambiguously determined.The existence of 1,2- and 1,4-dihydrotriazines, 20 and 22, described in the literature was ruled out.Irradiation of the aromatic triazines 6 and 15 and the novel quaternary dihydro-1,2,4-triazinium salts 4, 5, 19 furnished new evidence for both the reduction pathways and the mechanism of ring-contraction reactions.